5-溴吡咯-3-甲醛

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: By a similar operation as in Reference Example 148 and using 5-bromo-1H-pyrrole-3-carbaldehyde (870 mg), (2-bromophenyl)boronic acid (1.20 g), sodium carbonate (1.27 g) and tetrakis(triphenylphosphine)palladium (289 mg), the title compound was obtained as colorless crystals (yield 396 mg, 32%).

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

实验步骤: By a similar operation as in Reference Example 148 and using 5-bromo-1H-pyrrole-3-carbaldehyde (870 mg), (2-bromophenyl)boronic acid (1.20 g), sodium carbonate (1.27 g) and tetrakis(triphenylphosphine)palladium (289 mg), the title compound was obtained as colorless crystals (yield 396 mg, 32%).

反应条件: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5-Bromo-1H-pyrrole-3-carbaldehyde (174 mg), [2-(methylthio)phenyl]boronic acid (202 mg) and sodium carbonate (254 mg) were suspended in a mixed solvent of 1,2-dimethoxyethane (5 mL) and water (2 mL), and the mixture was sufficiently degassed under a nitrogen atmosphere. Tetrakis(triphenylphosphine)palladium (58 mg) was added, and the mixture was further degassed and stirred at 105° C. for 16 hr. The reaction mixture was allowed to cool to room temperature, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→4:1) to give the title compound as pale-yellow crystals (yield 150 mg, 69%). the mixture was sufficiently degassed under a nitrogen atmosphere Tetrakis(triphenylphosphine)palladium (58 mg) was added the mixture was further degassed to cool to room temperature water was added the mixture was extracted with ethyl acetate The extract was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→4:1)

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

实验步骤: A mixture of 5-bromo-1H-pyrrole-3-carbaldehyde (0.87 g), 2,4,6-trimethylphenylboronic acid (3.28 g), cesium carbonate (13.0 g), tri-tert-butylphosphine (0.10 g), tris(dibenzylideneacetone)dipalladium (0) (0.23 g) and mesitylene (200 mL) was stirred with heating under reflux for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:1) to give the title compound as a brown amorphous form (yield 0.30 g, 28%). with heating under reflux for 5 hr the mixture was extracted with ethyl acetate The extract was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:1)

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

实验步骤: A mixture of 5-bromo-1H-pyrrole-3-carbaldehyde (0.87 g), 2,4,6-trimethylphenylboronic acid (3.28 g), cesium carbonate (13.0 g), tri-tert-butylphosphine (0.10 g), tris(dibenzylideneacetone)dipalladium (0) (0.23 g) and mesitylene (200 mL) was stirred with heating under reflux for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:1) to give the title compound as a brown amorphous form (yield 0.30 g, 28%). with heating under reflux for 5 hr the mixture was extracted with ethyl acetate The extract was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:1)

反应条件: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5-Bromo-1H-pyrrole-3-carbaldehyde (100 mg), 2-methylphenylboronic acid (94 mg) and sodium carbonate (146 mg) were suspended in a mixed solvent of 1,2-dimethoxyethane (5 mL) and water (2 mL), and the mixture was sufficiently degassed under a nitrogen atmosphere. Tetrakis(triphenylphosphine)palladium (33 mg) was added, and the mixture was further degassed and refluxed at 105° C. for 24 hr. The reaction mixture was allowed to cool to room temperature, and the mixture was extracted with water and ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=8:1→3:1) to give the title compound as colorless crystals (yield 72 mg, 68%). the mixture was sufficiently degassed under a nitrogen atmosphere Tetrakis(triphenylphosphine)palladium (33 mg) was added the mixture was further degassed to cool to room temperature the mixture was extracted with water and ethyl acetate The extract was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=8:1→3:1)

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

实验步骤: 投料: 2025-10-29 11：30 称取SM1（10g 57.5mmol 1.0eq）于250ml三口瓶中，加入DMF使其完全溶解，后依次加入碳酸钠（15.24g 143.68mmol 2.5eq），SM2（8.86g 63.22mmol 1.1eq），四（三苯基膦）钯（6.7g 5.8mmol0.1eq），抽充氮气三次，升至110℃搅拌过夜。 2025-10-30 12：00 补加碳酸钠（7.6g），SM2（1.14g），四（三苯基膦）钯（3.32g），并加入水（用N2吹气）20ml，抽充氮气三次，升至110℃搅拌过夜。\n监测: 2025-10-29 13：43 LC-MS：102037-R，TLC：PE:EA=1：1，rf =0.8。 2025-10-29 16：41 LC-MS：102037-R2，有新点生成，但无目标产物。 2025-10-30 09：10 LC-MS：102037-R3。 2025-10-30 13：54 LC-MS：102037-R4，有新点生成，有目标产物生成。 2025-10-30 16：39 LC-MS：102037-R5。 2025-10-30 17：03 LC-MS：102037-B。 2025-10-31 09：10 LC-MS：102037-R6，原料基本反应完全，有目标产物生成。\n后处理: 2025-10-31 10：30 将反应液进行降温，后垫硅藻土过滤反应液，用EA洗涤滤饼。旋干滤液，用EA进行萃取，重复操作2~3次，合并有机相，用无水硫酸钠进行干燥，旋干后拌样过柱。\n纯化: 2025-10-31 14：30 过正相柱对产物进行纯化分离，以PE，EA作为流动相，硅胶粉作为固定相，洗脱梯度依次为纯PE、PE:EA=100：1~1：1，其中当洗脱梯度为PE:EA=10：1时，出目标产物峰，每五管进行TLC点板监测，有杂质点，全部收集旋干，得到深褐色固体。\n纯化: 2025-11-03 11：00 过正相柱对产物进行纯化分离，以PE，EA作为流动相，硅胶粉作为固定相，洗脱梯度依次为纯PE、PE:EA=100：1~1：1，其中当洗脱梯度为PE:EA=4：1时，出目标产物峰，每五管进行TLC点板监测，有杂质点，将干净与不干净的分批收集旋干，其中得到干净的1.5g，性状为类白色固体；不干净的2.5g，性状为淡黄色固体。 2025-11-04 11：00 过反相柱对产物进行纯化分离，用水，乙腈作为洗脱剂，通过LC-MS对纯化产物进行监测，其中当洗脱梯度为13%时，出杂质峰；当洗脱梯度为45%时，出现目标产物峰，各峰送检LC-MS，无杂质点，收集旋干，得到类白色固体。 2025-11-05 10：00 送检三谱和定量合格，最终入库3.2g，性状为类白色固体。