反応 #1483074

反応方程式

dioxane

1-methyl-1H-indole-5-carboxylic acid methyl ester

4-nitro-benzyl bromide

4-nitro-benzyl bromide

→

1-methyl-3-(4-nitro-phenylmethyl)-1H-indole-5-carboxylic acid methyl ester

収率 58.6%

溶媒

ether

ethyl acetate

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度to reflux for 25 hr
3. 3
   温度the solution was heated
4. 4
   温度at reflux an additional 4 days
5. 5
   洗浄washed with aq. NH4Cl (50 mL)
6. 6
   乾燥The organic layer was dried over MgSO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated

実験手順

A solution of 1-methyl-1H-indole-5-carboxylic acid methyl ester (0.38 g, 2.0 mmol), prepared using procedures as described in Example 1, Ag2O (0.51 g, 2.2 mmol), 4-nitro-benzyl bromide (0.48 g, 2.2 mmol) and dioxane (6 mL) was heated to reflux for 25 hr, then more 4-nitro-benzyl bromide (0.48 g, 2.2 mmol) was added and the solution was heated at reflux an additional 4 days. After cooling to room temperature, the reaction mixture was diluted with ether (50 mL) and ethyl acetate (50 mL), washed with aq. NH4Cl (50 mL) and then brine (50 mL). The organic layer was dried over MgSO4, filtered and concentrated. The remaining residue was subjected to flash chromatography (ethyl acetate/hexane, 1:4) to provide of 1-methyl-3-(4-nitro-phenylmethyl)-1H-indole-5-carboxylic acid methyl ester (0.38 g, 58% yield). 1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 8.16 (d, 2H, J=8.3 Hz), 7.98 (d, 1H, J=8.3 Hz), 7.45 (d, 2H, J=8.3 Hz), 7.35 (d, 1H, J=8.3 Hz), 6.90 (s, 1H), 4.25 (s, 2H), 3.94 (s, 3H), 3.82 (s, 3H).

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