丁基硼酸

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

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: A 4 ml vial was charged with 4-tert-butylbromobenzene (1.00 mmol), Pd(dba)2 (0.01 mmol, 1 mol %), Ph5FcP(t-Bu)2 (0.02 mmol, 2 mol %), KF (2.02 mmol, powdered) and n-butylboronic acid (1.21 mmol). Anhydrous THF (2 ml) and a stirring bar were added, and the vial was sealed with a cap containing a PTFE septum and removed from the drybox. The reaction mixture was stirred at room temperature for 18 h. After a starting aryl halide was consumed as determined by GC, the reaction solution was cooled to room temperature. Then the reaction solution was adsorbed onto silica gel directly, and the product was isolated by eluting with ethyl acetate/hexanes to give 220 mg (98%) of 4-tert-butyl-1-n-butylbenzene as a colorless oil. Kugelrohl distillation was used for further purification. the vial was sealed with a cap removed from the drybox After a starting aryl halide was consumed the reaction solution was cooled to room temperature the product was isolated by eluting with ethyl acetate/hexanes

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 4 mL vial was charged with 4-tert-butylbromobenzene (213 mg, 1.00 mmol), Pd(dba)2 (5.8 mg, 0.01 mmol, 1 mol %), Ph5FcP(t-Bu)2 (14.2 mg, 0.02 mmol, 2 mol %), K3PO4 (430 mg, 2.02 mmol, powdered) and n-butylboronic acid (124 mg, 1.21 mmol). Anhydrous toluene (2 mL) and a stirring bar were added, and the vial was then sealed with a cap containing a PTFE septum and removed from the drybox. The reaction mixture was stirred at 100° C. for 2.5 h. After the starting aryl halide was consumed as determined by GC, the reaction solution was cooled to room temperature. The reaction solution was then adsorbed onto silica gel directly, and the product was isolated by eluting with ethyl acetate/hexanes to give 175 mg (92%) of 4-tert-butyl-1-n-butylbenzene as colorless oil. Kugelrohl distillation was used for further purification. the vial was then sealed with a cap removed from the drybox After the starting aryl halide was consumed the reaction solution was cooled to room temperature the product was isolated by eluting with ethyl acetate/hexanes

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

实验步骤: A solution of ethyl [4-bromo-2-(1-phenyl-1H-pyrazole-4-carbonyl)phenoxy]acetate (472 mg, 1.1 mmol), 1-butylboronic acid (102 mg, 1.0 mmol) and Pd (dppf)Cl2 (72 mg, 0.05 mmol) in THF (10 mL) and water (1 mL) under argon was refluxed for 24 h. The reaction mixture was extracted with CH2Cl2, the organic phase was filtered through celite and concentrated, and the residue was purified by flash chromatography (SiO2, EtOAc:heptane, 1:10 to 1:1). The purest fraction was concentrated (˜10 mg), and the residue was hydrolysed according to GP3: LC/MS (an 10p8): Rt 2.59 min, m/z 379.1 [M+H]+; 1H NMR (CDCl3): δ 0.88 (t, J=7.5 Hz, 3H), 1.29 (m, 2H), 1.49 (m, 2H), 2.48 (m, 2H), 4.51 (s, 2H), 6.84 (m, 1H), 7.14 (m, 1H), 7.30 (m, 2H), 7.42 (m, 2H), 7.65 (m, 2H), 7.97 (s, 1H), 8.46 (s, 1H). The reaction mixture was extracted with CH2Cl2 the organic phase was filtered through celite and concentrated the residue was purified by flash chromatography (SiO2, EtOAc:heptane, 1:10 to 1:1) The purest fraction was concentrated (˜10 mg)

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

实验步骤: A mixture of 3-(4-bromophenyl)-2-(2-chlorophenyl)-5-methyl-6-(2,2,2-trifluoroethyl)-2,6-dihydropyrazolo[4,3-d]pyrimidin-7-one (4A-9, 48.4 mg, 0.1 mmol), 1-butane boronic acid (12 mg, 0.12 mmol), K2CO3 (41 mg, 0.3 mmol), PdCl2dppf.CH2Cl2 (8 mg, 0.01 mmol) in THF (2 ml) was heated at 65° C. for 18 h. The reaction mixture was cooled to room temperature, diluted with H2O, and extracted with EtOAc (2×). The combined extracts were washed with 0.5 M citric acid, saturated aqueous NaCl, dried, and concentrated under vacuum. The crude residue was purified on a Chromatotron using 1 mm plates and 25% EtOAc/hexanes as a solvent to give 8A-1 (16 mg): MS (m/z) 475.5 (M+H)+; 1H NMR (400 MHz, CDCl3): δ 7.53-7.49 (m, 1H), 7.47-7.36 (m, 3H), 7.31 (d, J=8.3 Hz, 2H), 7.12 (d, J=8.3 Hz, 2H), 4.98-4.78 (br m, 2H), 2.60 (s, 3H), 2.56 (t, J=7.5 Hz, 2H), 1.6-1.5 (m, 2H), 1.36-1.27 (m, 2H), 0.89 (t, J=7.5 Hz, 3H). extracted with EtOAc (2×) The combined extracts were washed with 0.5 M citric acid, saturated aqueous NaCl dried concentrated under vacuum The crude residue was purified on a Chromatotron to give 8A-1 (16 mg)

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (300 mg), n-butylboronic acid (340 mg), tetrakis(triphenylphosphine)palladium(0) (80 mg), potassium carbonate (280 mg), toluene (6 ml) and THF (3 ml) was stirred at 100° C. under a nitrogen atmosphere for 12 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine. The solvent was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1) and crystallized from hexane to give the title compound (210 mg). the mixture was extracted with ethyl acetate The organic layer was washed with water and saturated brine The solvent was dried over anhydrous sodium sulfate concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1) crystallized from hexane

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (300 mg), n-butylboronic acid (340 mg), tetrakis(triphenylphosphine)palladium(0) (80 mg), potassium carbonate (280 mg), toluene (6 ml) and THF (3 ml) was stirred at 100° C. under a nitrogen atmosphere for 12 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine. The solvent was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1) and crystallized from hexane to give the title compound (210 mg). the mixture was extracted with ethyl acetate The organic layer was washed with water and saturated brine The solvent was dried over anhydrous sodium sulfate concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1) crystallized from hexane

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

实验步骤: A mixture of 3-(4-bromophenyl)-2-(2-chlorophenyl)-5-methyl-6-(2,2,2-trifluoroethyl)-2,6-dihydropyrazolo[4,3-d]pyrimidin-7-one (4A-9, 48.4 mg, 0.1 mmol), 1-butane boronic acid (12 mg, 0.12 mmol), K2CO3 (41 mg, 0.3 mmol), PdCl2dppf.CH2Cl2 (8 mg, 0.01 mmol) in THF (2 ml) was heated at 65° C. for 18 h. The reaction mixture was cooled to room temperature, diluted with H2O, and extracted with EtOAc (2×). The combined extracts were washed with 0.5 M citric acid, saturated aqueous NaCl, dried, and concentrated under vacuum. The crude residue was purified on a Chromatotron using 1 mm plates and 25% EtOAc/hexanes as a solvent to give 8A-1 (16 mg): MS (m/z) 475.5 (M+H)+; 1H NMR (400MHz, CDCl3): δ 7.53–7.49 (m, 1H), 7.47–7.36 (m, 3H), 7.31 (d, J=8.3 Hz, 2H), 7.12 (d, J=8.3 Hz, 2H), 4.98–4.78 (br m, 2H), 2.60 (s, 3H), 2.56 (t, J=7.5 Hz, 2H), 1.6–1.5 (m, 2H), 1.36–1.27 (m, 2H), 0.89 (t, J=7.5 Hz, 3H). extracted with EtOAc (2×) The combined extracts were washed with 0.5 M citric acid, saturated aqueous NaCl dried concentrated under vacuum The crude residue was purified on a Chromatotron to give 8A-1 (16 mg)

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

实验步骤: To a solution of 2,2′-azanediyldiethanol (26.12 g, 246 mmol) in DCM (250 ml) and ether (500 mL) was added n-butylboronic acid (25.4 g, 242 mmol) and molecular sieves (3 A, 4-6 mesh, 65 g). It was stirred at ambient temperature for 2 hours. The mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting white solid was recrystallized with DCM/ether to provide white crystals as the title product. NMR (300 MHz, CDCl3): δ 0.47 (t, J=9 Hz, 2H), 0.88 (t, J=6 Hz, 3H), 1.20-1.37 (m, 4H), 2.82 (br, 2H), 3.24 (br, 2H), 3.95 (br, 4H), 4.27 (br, 1H). MS (DCI—NH3) m/z 172 (M+H)+. The mixture was filtered the filtrate was concentrated under reduced pressure The resulting white solid was recrystallized with DCM/ether

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

实验步骤: To a solution of 2,2′-azanediyldiethanol (26.12 g, 246 mmol) in DCM (250 ml) and ether (500 mL) was added n-butylboronic acid (25.4 g, 242 mmol) and molecular sieves (3A, 4-6 mesh, 65 g). It was stirred at ambient temperature for 2 hours. The mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting white solid was recrystallized with DCM/ether to provide white crystals as the title product. NMR (300 MHz, CDCl3): δ 0.47 (t, J=9 Hz, 2H), 0.88 (t, J=6 Hz, 3H), 1.20-1.37 (m, 4H), 2.82 (br, 2H), 3.24 (br, 2H), 3.95 (br, 4H), 4.27 (br, 1H). MS (DCl—NH3) m/z 172 (M+H)+. The mixture was filtered the filtrate was concentrated under reduced pressure The resulting white solid was recrystallized with DCM/ether