反応 #1359393

反応方程式

4-bromobenzamide

sodium carbonate

potassium acetate

trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester

bis(pinacolato)diboron

→

{2-[7-(4-carbamoyl-phenyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester

収率 58.5%

溶媒

dimethylsulfoxide

brine

ethyl acetate

反応条件

後処理

1. 1
   温度The mixture is cooled to 20° C.
2. 2
   workup.ADDITIONare added
3. 3
   温度The mixture is heated to 80° C. overnight
4. 4
   洗浄The organic fraction is washed seven times with brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   ろ過filtered
7. 7
   その他evaporated
8. 8
   その他The residue is purified
9. 9
   洗浄silica gel chromatography (dichloromethane/10% methanol, 0.7M ammonia in dichloromethane gradient elution)

実験手順

A solution of 4-bromobenzamide (150 mg, 0.75 mmol), bis(pinacolato)diboron (209 mg, 0.825 mmol), potassium acetate (0.221 g, 2.25 mmol) and {1,1′-bis(diphenylphosphino)-ferrocene} dichloropalladium dichloromethane complex (18 mg, 0.0225 mmol) in dimethylsulfoxide (5 mL) is heated to 80° C. for two hours. The mixture is cooled to 20° C. and trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester (262 mg, 0.600 mmol), {1,1′-bis(diphenylphosphino)-ferrocene} dichloropalladium dichloromethane complex (18 mg, 0.0225 mmol) and sodium carbonate (1.9 mL, 2M, 3.75 mmol) are added. The mixture is heated to 80° C. overnight. The mixture is diluted with brine and ethyl acetate. The organic fraction is washed seven times with brine, then dried over anhydrous sodium sulfate, filtered and evaporated. The residue is purified using silica gel chromatography (dichloromethane/10% methanol, 0.7M ammonia in dichloromethane gradient elution) to give 143 mg of {2-[7-(4-carbamoyl-phenyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (58%). FDMS m/e=408 (M++1).

出典