반응 #1483079

반응 방정식

4-fluoro-benzyl bromide

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

4-fluoro-benzyl bromide

dioxane

→

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

수율 22.0%

용매

ether

반응 조건

후처리

1. 1
   온도were heated
2. 2
   온도to reflux for 16 hr
3. 3
   온도the solution was heated
4. 4
   온도at reflux an additional 4 hr
5. 5
   세척washed with aq. NH4Cl (50 mL)
6. 6
   건조The organic layer was dried over MgSO4
7. 7
   여과filtered
8. 8
   농축concentrated

실험 절차

A solution of 1-methyl-1H-indole-5-carboxylic acid methyl ester (0.17 g, 0.9 mmol), prepared using procedures as described in Example 1, Ag2O) (0.22 g, 0.95 mmol), 4-fluoro-benzyl bromide (0.18 g, 0.95 mmol) and dioxane (4 mL) were heated to reflux for 16 hr, then more 4-fluoro-benzyl bromide (90 mg, 0.5 mmol) was added and the solution was heated at reflux an additional 4 hr. After cooling to room temperature, the reaction mixture was diluted with ether (60 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, 1:3) to provide 3-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester (58 mg, 22% yield).

출처