反应详情

温度

-78 °C

To a solution of benzyloxymethyllithium in THF (2 mL, prepared from n-Bu3SnCH2OBn (505 mg, 1.23 mmol) and n-BuLi (0.49 mL, 1.22 mmol, 2.5 M solution in hexane) by the procedure reported in J. Am. Chem. Soc. 1978, 100, 1481) is added a solution of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carbaldehyde 10f (51 mg, 0.14 mmol) in THF (3 mL) at −78° C. The resulting solution is stirred for 1 hour at −78° C. The reaction is quenched with saturated aqueous NH4Cl, and extracted with EtOAc. The organic layer is dried over MgSO4, filtered, concentrated in vacuo, and purified by flash chromatography (100% CH2Cl2 to 3% MeOH in CH2Cl2) to afford the desired product (46 mg, 68%): MS APCI (+) m/z 490, 492 (M+, Br pattern) detected.

1. customThe reaction is quenched with saturated aqueous NH4Cl
2. extractionextracted with EtOAc
3. dry with materialThe organic layer is dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. custompurified by flash chromatography (100% CH2Cl2 to 3% MeOH in CH2Cl2)