반응 #88093

반응 방정식

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

5-methyl-pyridinyl zinc bromide

→

3-Isobutyl-7-(5-methyl-pyridin-2-yl)-3H-benzoimidazole-5-carboxylic acid methyl ester

수율 57.2%

용매

THF

반응 조건

후처리

1. 1
   기타quenched by addition of saturated aqueous NH4Cl solution
2. 2
   기타The mixture was partitioned between water and ethyl acetate
3. 3
   기타the organic layer was separated
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure
7. 7
   기타Purification by column chromatography

실험 절차

To a solution of 7-iodo-3-isobutyl-3H-benzoimidazole-5-carboxylic acid methyl ester (400 mg, 1.12 mmol) in THF (4 mL) was added Pd(PPh3)4 (65 mg, 0.056 mmol), followed by 5-methyl-pyridinyl zinc bromide (2.68 mL of 0.5M solution in THF, 1.34 mmol). The reaction mixture was stirred overnight at room temperature, then quenched by addition of saturated aqueous NH4Cl solution. The mixture was partitioned between water and ethyl acetate, and the organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by column chromatography gave 207 mg (57%) of 3-Isobutyl-7-(5-methyl-pyridin-2-yl)-3H-benzoimidazole-5-carboxylic acid methyl ester.

출처