반응 #88092

반응 방정식

isobutyl bromide

7-iodo-3H-benzoimidazole-5-carboxylic acid methyl ester

Cs2CO3

→

7-iodo-3-isobutyl-3H-benzoimidazole-5-carboxylic acid methyl ester

수율 87.0%

7-iodo-1-isobutyl-1H-benzoimidazole-5-carboxylic acid methyl ester

수율 11.0%

용매

DMF

반응 조건

후처리

1. 1
   기타partitioned between water and ethyl acetate
2. 2
   기타The organic layer was separated
3. 3
   건조dried over MgSO4
4. 4
   여과filtered
5. 5
   농축concentrated under reduced pressure
6. 6
   기타Purification of the residue by column chromatography

실험 절차

To a solution of 7-iodo-3H-benzoimidazole-5-carboxylic acid methyl ester (783 mg, 2.59 mmol) in DMF (50 mL) was added Cs2CO3 (1.69 g, 5.18 mmol), followed by isobutyl bromide ((0.338 mL, 3.11 mmol). The reaction mixture was stirred room temperature overnight, then partitioned between water and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by column chromatography gave 805 mg (87%) of 7-iodo-3-isobutyl-3H-benzoimidazole-5-carboxylic acid methyl ester (the regioisomer 7-iodo-1-isobutyl-1H-benzoimidazole-5-carboxylic acid methyl ester (100 mg, 11%) was recovered as separate fraction).

출처