4-氨基-2-甲氧基苯酚

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: To a solution of (2E)-3-{3-cyano-4,6-dimethyl-1-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (300 mg, 0.808 mmol) in THF (3 ml) were added DMF (0.03 ml) and oxalylchloride (0.0846 ml, 0.970 mmol), the mixture was stirred at room temperature for 1 hour and the solvent was distilled off under reduced pressure. The residue was added under ice-cooling to a solution of 4-hydroxy-3-methoxyaniline (135 mg, 0.968 mmol), pyridine (0.262 ml, 3.24 mmol) and THF (3 ml), and the mixture was stirred under ice-cooling for 2 hours and at room temperature for 12 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the objective product as a solid material. the solvent was distilled off under reduced pressure The residue was added under ice- the mixture was stirred under ice- cooling for 2 hours and at room temperature for 12 hours extracted with ethyl acetate The extract was washed with water dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

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

实验步骤: This compound was prepared from 4-nitro-2-methoxyphenol (10.0 g, 59.1 mmol) in the manner described for 4-amino-3-fluorophenol, affording 5.20 g (56.9%) of 4-amino-2-methoxyphenol as a dark brown solid. 1H-NMR (DMSO-d6) δ 7.79 (br s, 1H), 6.44 (d, J=8.1 Hz, 1H), 6.21 (d, J=2.4 Hz, 1H), 5.97 (dd, J=8.4, 2.4 Hz, 1H), 4.43 (br s, 2H), 3.65 (s, 3H); TLC (66% EtOAc/Hex), Rf=0.42.

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

实验步骤: 6.85 g of 1,3-dimethyl-5-ethoxycarbonylbarbituric acid and 4.2 g of 4-hydroxy-3-methoxyaniline are suspended in 60 ml of toluene, and the suspension is heated under reflux for 3 hours, whereupon ethanol escapes. On cooling to room temperature a precipitate forms which is isolated by filtration, washed with ethanol and dried. Yield: 8.3 g (86% of theory). Melting point: 252°-253° C. the suspension is heated is isolated by filtration washed with ethanol dried

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

实验步骤: 6.85 g of 1,3-dimethyl-5-ethoxycarbonylbarbituric acid and 4.2 g of 4-hydroxy-3-methoxyaniline are suspended in 60 ml of toluene, and the suspension is heated under reflux for 3 hours, whereupon ethanol escapes. On cooling to room temperature a precipitate forms which is isolated by filtration, washed with ethanol and dried. Yield: 8.3 g (86% of theory). Melting point: 252°-253° C. the suspension is heated is isolated by filtration washed with ethanol dried

实验步骤: 投料: 向双口瓶，加入M-C4X-121116-SM1（30.0g，1.0eq）和THF（6V），降温0~10℃滴加加入乙酸酐（ 1.3eq），室温下搅拌2h。 LCMS/TLC（DCM:MEOH=10:1)检测（C4X-121116-1-R1），结果显示，原料反应完全，有产物ms生成，体系浓缩干，拌样柱层析（PE:EA=2;1出产物） 得29g，纯度97.5%，单杂2.1%，棕褐色固体

实验步骤: 投料: 向双口瓶，加入M-C4X-121116-SM1（3.0g，1.0eq）和THF（6V），降温0~10℃滴加加入乙酸酐（ 1.5eq），室温下搅拌2h。 LCMS检测（C4X-121116-186-109-IPC1），结果显示，原料反应完全，有产物ms生成

实验步骤: 投料: 取250ml干燥单口瓶，加入M-C4X-121116-SM1（15g 107.8mmol 1eq）和THF（50ml），室温下加入乙酸酐（20.5ml 215.6mmol 2eq），室温下搅拌4h。 LCMS检测（121116-S1-4），结果显示，原料反应完全，有产物ms生成 反应液旋掉溶剂后加水冻干，得到黑色固体 粗品经自动过柱机分离纯化（PE:EA=2：1），得到棕褐色固体13.5g

实验步骤: 放大: 向单口瓶中依次加入4-amino-2-methoxyphenol（4.23g，1.0 eq）、25mL DCM和acetic anhydride（6.21g，2.0 eq），室温下搅拌4h。LCMS监测产物生成且原料消失，TLC(PE：EA=1:1,Rf=0.4)，加15mL H2O冻干得5.3g 黑紫色固体产物。

实验步骤: 小试: 向单口瓶中依次加入4-amino-2-methoxyphenol（100mg，1.0 eq）、3mL DCM和acetic anhydride（147mg，2.0 eq），室温下搅拌2h。LCMS监测产物生成且原料消失，TLC(PE：EA=1:1,Rf=0.4)，加5mL H2O冻干得130mg 黑紫色固体产物。