Sodium borohydride → [6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-(2-methanesulfonyl-ethyl)-3H-benzoimidazol-5-yl]-methanol

6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-(2-methanesulfonyl-ethyl)-3H-benzoimidazole-5-carboxylic acid methyl ester 11 cc (0.300 g, 0.594 mmol) is suspended in a mixture of EtOH (6 mL) and THF (4 mL) under N2. NaBH4 (0.112 g, 2.97 mmol) is added. After approximately 4 days stirring, reaction mixture is quenched by the addition of AcOH until the reaction mixture reaches pH 7. The reaction mixture is concentrated to dryness under reduced pressure and the residue partitioned between ethyl acetate and water. The layers are separated and the organic layer is washed with water (3×), brine, and dried (Na2SO4). The organic layer is concentrated under reduced pressure until a white precipitate forms which is collected by filtration to give 0.225 g (79%) clean desired product: LC/MS ESI (+) m/z 478, 476 (M+ Br pattern) detected.

1. customreaction mixture
2. customis quenched by the addition of AcOH until the reaction mixture
3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
4. customthe residue partitioned between ethyl acetate and water
5. customThe layers are separated
6. washthe organic layer is washed with water (3×), brine
7. dry with materialdried (Na2SO4)
8. concentrationThe organic layer is concentrated under reduced pressure until a white precipitate forms which
9. filtrationis collected by filtration

ORDレコード

ord-19a8493078cd4f19affdc6ab0310f9d3

出典データセット

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08193231B2