تفاعل #1483079

معادلة التفاعل

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

المردود 22.0%

المذيبات

ether

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwere heated
2. 2
   درجة الحرارةto reflux for 16 hr
3. 3
   درجة الحرارةthe solution was heated
4. 4
   درجة الحرارةat reflux an additional 4 hr
5. 5
   غسيلwashed with aq. NH4Cl (50 mL)
6. 6
   تجفيفThe organic layer was dried over MgSO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated

الإجراء التجريبي

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).

المصدر