反応 #10839

反応方程式

5-bromo-2,4-dimethoxybenzaldehyde

H2O2

N-methyl indole

t-BuLi

NaOH

BEt3

→

2,4-dimethoxy-5-(1-methyl-1H-indol-2-yl)-benzaldehyde

収率 25.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture stirred for another 1 hr at room temperature
2. 2
   温度the mixture was heated to about 60° C. for 30 minutes
3. 3
   workup.STIRRINGstirred for 10 minutes
4. 4
   抽出The mixture was extracted with EtOAc and combined organic phase
5. 5
   洗浄was washed with H2O and brine
6. 6
   乾燥dried over MgSO4
7. 7
   その他absorbed to small amount of silica gel

実験手順

Ex-116A: To a solution of N-methyl indole (1.3 g, 10 mmol) in 50 ml THF, t-BuLi (1.7 m in THF, 7.1 ml, 12 mmol) was slowly added at 0° C. under nitrogen. The mixture was stirred at room temperature for 1 hr, BEt3 (1.0 M in THF, 12 ml, 12 mmol) was added, and the mixture stirred for another 1 hr at room temperature. Then, PdCl2(PPh3)2 (0.35 g, 0.5 mmol) and 5-bromo-2,4-dimethoxybenzaldehyde (3.7 g, 15 mmol) were added, and the mixture was heated to about 60° C. for 30 minutes. The reaction mixture was poured into 50 ml 10% NaOH and treated with 30% H2O2 and then stirred for 10 minutes. The mixture was extracted with EtOAc and combined organic phase was washed with H2O and brine, dried over MgSO4, and absorbed to small amount of silica gel. Column chromatography (EtOAc:Hexane, 1:2) gave 0.72 g (25%) 2,4-dimethoxy-5-(1-methyl-1H-indol-2-yl)-benzaldehyde. 1H-NMR (CDCl3) δ 10.33 (s, 1H), 7.84 (s, 1H), 7.60 (d, J=8 Hz, 1H), 7.31 (d, J=8 Hz, 1H), 7.18–7.24 (m, 1H), 7.07–7.12 (m, 1H), 6.53 (s, 1H), 6.46 (s, 1H), 4.00 (s, 3H), 3.89 (s, 3H), 3.53 (s, 3H). HRMS (EI) Calcd. for C18H17NO3: 295.1208. Found: 295.1202.

出典