4-碘-N,N-二甲基苯磺酰胺

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Dimethylamine (100 mL of 2.0 M solution in tetrahydrofuran; 200 mmol) was added to a solution of 4-iodobenzenesulfonyl chloride (54.76 g; 181 mmol) in pyridine (300 mL) at 0° C. under N2, followed by the addition of 4-N,N-dimethylaminopyridine (15 mg). The reaction was allowed to warm to room temperature and was stirred under N2 for 48 hrs. The reaction solution was poured into 1.2 liter of water, and the precipitated product was collected by filtration and rinsed with water (300 mL×2). The solid was dissolved in ethyl acetate (500 mL) and washed with 5% aqueous hydrochloric acid (300 mL×3), water (300 mL×2) and brine (300 mL). The organic solution was dried over anhydrous sodium sulfate and concentrated to give 4-iodo-N,N-dimethyl-benzenesulfonamide (49.46 g; 88%) as a white solid, which was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) δ 7.88 (d, 2H, J=8.5 Hz), 7.46 (d, 2H, J=8.5 Hz), 2.69 (s, 3H). the precipitated product was collected by filtration rinsed with water (300 mL×2) The solid was dissolved in ethyl acetate (500 mL) washed with 5% aqueous hydrochloric acid (300 mL×3), water (300 mL×2) and brine (300 mL) The organic solution was dried over anhydrous sodium sulfate concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Dimethylamine (100 mL of 2.0 M solution in tetrahydrofuran; 200 mmol) was added to a solution of 4-iodobenzenesulfonyl chloride (54.76 g; 181 mmol) in pyridine (300 mL) at 0° C. under N2, followed by the addition of 4-N,N-dimethylaminopyridine (15 mg). The reaction was allowed to warm to room temperature and was stirred under N2 for 48 hrs. The reaction solution was poured into 1.2 liter of water, and the precipitated product was collected by filtration and rinsed with water (300 mL×2). The solid was dissolved in ethyl acetate (500 mL) and washed with 5% aqueous hydrochloric acid (300 mL×3), water (300 mL×2) and brine (300 mL). The organic solution was dried over anhydrous sodium sulfate and concentrated to give 4-iodo-N,N-dimethyl-benzenesulfonamide (49.46 g; 88%) as a white solid, which was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) δ 7.88 (d, 2H, J=8.5 Hz), 7.46 (d, 2H, J=8.5 Hz), 2.69 (s, 3H). the precipitated product was collected by filtration rinsed with water (300 mL×2) The solid was dissolved in ethyl acetate (500 mL) washed with 5% aqueous hydrochloric acid (300 mL×3), water (300 mL×2) and brine (300 mL) The organic solution was dried over anhydrous sodium sulfate concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Dimethylamine (100 mL of 2.0 M solution in tetrahydrofuran; 200 mmol) was added to a solution of 4-iodobenzenesulfonyl chloride (54.76 g; 181 mmol) in pyridine (300 mL) at 0° C. under N2, followed by the addition of 4-N,N-dimethylaminopyridine (15 mg). The reaction was allowed to warm to room temperature and was stirred under N2 for 48 hrs. The reaction solution was poured into 1.2 liter of water, and the precipitated product was collected by filtration and rinsed with water (300 mL×2). The solid was dissolved in ethyl acetate (500 mL) and washed with 5% aqueous hydrochloric acid (300 mL×3), water (300 mL×2) and brine (300 mL). The organic solution was dried over anhydrous sodium sulfate and concentrated to give 4-iodo-N,N-dimethyl-benzenesulfonamide (49.46 g; 88%) as a white solid, which was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) δ 7.88 (d, 2H, J=8.5 Hz), 7.46 (d, 2H, J=8.5 Hz), 2.69 (s, 3H). the precipitated product was collected by filtration rinsed with water (300 mL×2) The solid was dissolved in ethyl acetate (500 mL) washed with 5% aqueous hydrochloric acid (300 mL×3), water (300 mL×2) and brine (300 mL) The organic solution was dried over anhydrous sodium sulfate concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Dimethylamine (100 mL of 2.0 M solution in tetrahydrofuran; 200 mmol) was added to a solution of 4-iodobenzenesulfonyl chloride (54.76 g; 181 mmol) in pyridine (300 mL) at 0° C. under N2, followed by the addition of 4-N,N-dimethylaminopyridine (15 mg). The reaction was allowed to warm to room temperature and was stirred under N2 for 48 hrs. The reaction solution was poured into 1.2 liter of water, and the precipitated product was collected by filtration and rinsed with water (300 mL×2). The solid was dissolved in ethyl acetate (500 mL) and washed with 5% aqueous hydrochloric acid (300 mL×3), water (300 mL×2) and brine (300 mL). The organic solution was dried over anhydrous sodium sulfate and concentrated to give 4-iodo-N,N-dimethyl-benzenesulfonamide (49.46 g; 88%) as a white solid, which was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) δ 7.88 (d, 2H, J=8.5 Hz), 7.46 (d, 2H, J=8.5 Hz), 2.69 (s, 3H). the precipitated product was collected by filtration rinsed with water (300 mL×2) The solid was dissolved in ethyl acetate (500 mL) washed with 5% aqueous hydrochloric acid (300 mL×3), water (300 mL×2) and brine (300 mL) The organic solution was dried over anhydrous sodium sulfate concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Dimethylamine (100 mL of 2.0 M solution in tetrahydrofuran; 200 mmol) was added to a solution of 4-iodobenzenesulfonyl chloride (54.76 g; 181 mmol) in pyridine (300 mL) at 0° C. under N2, followed by the addition of 4-N,N-dimethylaminopyridine (15 mg). The reaction was allowed to warm to room temperature and was stirred under N2 for 48 hrs. The reaction solution was poured into 1.2 liter of water, and the precipitated product was collected by filtration and rinsed with water (300 mL×2). The solid was dissolved in ethyl acetate (500 mL) and washed with 5% aqueous hydrochloric acid (300 mL×3), water (300 mL×2) and brine (300 mL). The organic solution was dried over anhydrous sodium sulfate and concentrated to give 4-iodo-N,N-dimethyl-benzenesulfonamide (49.46 g; 88%) as a white solid, which was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) δ 7.88 (d, 2H, J=8.5 Hz), 7.46 (d, 2H, J=8.5 Hz), 2.69 (s, 3H). the precipitated product was collected by filtration rinsed with water (300 mL×2) The solid was dissolved in ethyl acetate (500 mL) washed with 5% aqueous hydrochloric acid (300 mL×3), water (300 mL×2) and brine (300 mL) The organic solution was dried over anhydrous sodium sulfate concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Dimethylamine (100 mL of 2.0 M solution in tetrahydrofuran; 200 mmol) was added to a solution of 4-iodobenzenesulfonyl chloride (54.76 g; 181 mmol) in pyridine (300 mL) at 0° C. under N2, followed by the addition of 4-N,N-dimethylaminopyridine (15 mg). The reaction was allowed to warm to room temperature and was stirred under N2 for 48 hrs. The reaction solution was poured into 1.2 liter of water, and the precipitated product was collected by filtration and rinsed with water (300 mL×2). The solid was dissolved in ethyl acetate (500 mL) and washed with 5% aqueous hydrochloric acid (300 mL×3), water (300 mL×2) and brine (300 mL). The organic solution was dried over anhydrous sodium sulfate and concentrated to give 4-iodo-N,N-dimethyl-benzenesulfonamide (49.46 g; 88%) as a white solid, which was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) δ 7.88 (d, 2H, J=8.5 Hz), 7.46 (d, 2H, J=8.5 Hz), 2.69 (s, 3H). the precipitated product was collected by filtration rinsed with water (300 mL×2) The solid was dissolved in ethyl acetate (500 mL) washed with 5% aqueous hydrochloric acid (300 mL×3), water (300 mL×2) and brine (300 mL) The organic solution was dried over anhydrous sodium sulfate concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Dimethylamine (100 mL of 2.0 M THF solution; 200 mmol) was added to a solution of pipsyl chloride (54.76 g; 181 mmol) in pyridine (300 mL) at 0° C. under N2, followed by the addition of N,N-dimethylaminopyridine (15 mg). The reaction was stirred under N2 for two days while it warmed from 0° C. to room temperature. The reaction solution was poured into 1.2 liter of water. The desired product was precipitated out of the H2O/pyridine solution. The solid was collected by filtration and rinsed by H2O (300 mL×2). The solid was dissolved in EtOAc (500 mL). The EtOAc solution was washed by 5% aqueous HCl (300 mL×3), water (300 mL×2) and brine (300 mL×1), dried by Na2SO4 and concentrated to give 4-iodo-N,N-dimethylbenzenesulfonamide (49.46 g; 88%) as white solid, which was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) δ 7.88 (d, 2H, J=8.5 Hz), 7.46 (d, 2H, J=8.5 Hz), 2.69 (s, 3H). warmed from 0° C. to room temperature The desired product was precipitated out of the H2O/pyridine solution The solid was collected by filtration rinsed by H2O (300 mL×2) The solid was dissolved in EtOAc (500 mL) The EtOAc solution was washed by 5% aqueous HCl (300 mL×3), water (300 mL×2) and brine (300 mL×1) dried by Na2SO4 concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Dimethylamine (100 mL of 2.0 M THF solution; 200 mmol) was added to a solution of pipsyl chloride (54.76 g; 181 mmol) in pyridine (300 mL) at 0° C. under N2, followed by the addition of N,N-dimethylaminopyridine (15 mg). The reaction was stirred under N2 for two days while it warmed from 0° C. to room temperature. The reaction solution was poured into 1.2 liter of water. The desired product was precipitated out of the H2O/pyridine solution. The solid was collected by filtration and rinsed by H2O (300 mL×2). The solid was dissolved in EtOAc (500 mL). The EtOAc solution was washed by 5% aqueous HCl (300 mL×3), water (300 mL×2) and brine (300 mL×1), dried by Na2SO4 and concentrated to give 4-iodo-N,N-dimethylbenzenesulfonamide (49.46 g; 88%) as white solid, which was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) δ 7.88 (d, 2H, J=8.5 Hz), 7.46 (d, 2H, J=8.5 Hz), 2.69 (s, 3H). warmed from 0° C. to room temperature The desired product was precipitated out of the H2O/pyridine solution The solid was collected by filtration rinsed by H2O (300 mL×2) The solid was dissolved in EtOAc (500 mL) The EtOAc solution was washed by 5% aqueous HCl (300 mL×3), water (300 mL×2) and brine (300 mL×1) dried by Na2SO4 concentrated

反应条件: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 4-iodo-N,N-dimethylbenzenesulfonamide (156 mg, 0.5 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (105 mg, 0.55 mmol), copper (I) iodide (1 mol %, 1 mg, 0.005 mmol), trans-1,2-diaminocyclohexane (10 mol %, 6 mg, 0.05 mmol) and potassium carbonate (145 mg, 1.05 mmol) in 1,4-dioxane (1 ml) was stirred at 180° C. in a microwave reactor for 45 minutes. The reaction mix was cooled and added to a 5 g pre-packed silica column which was then eluted from ethyl acetate, the product was further purified by mass directed auto-prep to give a crop of the title compound as a pale beige solid (65 mg, 35%). The reaction mix was cooled added to a 5 g pre-packed silica column which was then eluted from ethyl acetate the product was further purified by mass

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared from pipsyl chloride and dimethylamine hydrochloride using a similar procedure to that used for Description 1.

反应条件: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 4-iodo-N,N-dimethylbenzenesulfonamide (156 mg, 0.5 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (105 mg, 0.55 mmol), copper (I) iodide (1 mol %, 1 mg, 0.005 mmol), trans-1,2-diaminocyclohexane (10 mol %, 6 mg, 0.05 mmol) and potassium carbonate (145 mg, 1.05 mmol) in 1,4-dioxane (1 ml) was stirred at 180° C. in a microwave reactor for 45 minutes. The reaction mix was cooled and added to a 5 g pre-packed silica column which was then eluted from ethyl acetate, the product was further purified by mass directed auto-prep to give a crop of the title compound as a pale beige solid (65 mg, 35%). The reaction mix was cooled added to a 5 g pre-packed silica column which was then eluted from ethyl acetate the product was further purified by mass