Sodium hydride → [3-(3-Chloro-pyrazin-2-YL)-azetidin-1-YL]-[1-(2,2,2-trifluoro-ethyl)-1H-benzoimidazol-2-YL]-methanone

To a solution of (1H-benzoimidazol-2-yl)-[3-(3-chloro-pyrazin-2-yl)-azetidin-1-yl]-methanone (84), as prepared in Preparation 36 below, (314 mg, 1.0 mmol) in dry DMF (10 mL) was added sodium hydride (applied as 60% dispersion in oil, 62 mg, 1.5 mmol)) at 0° C. under N2 atmosphere. After 0.5 h, 1,1,1-Trifluoro-2-iodo-ethane (418 mg, 2.0 mmol) was added slowly. The reaction mixture was stirred at RT for 4 h. The reaction was quenched with water (10 mL) at 0° C. and extracted with EtOAc (3×20 mL). The combined organics were washed with water (2×15 mL), brine (20 mL), dried over sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by flash column chromatography to provide (85) (355 mg, 0.90 mmol, 90% yield) as white solid.

1. customThe reaction was quenched with water (10 mL) at 0° C.
2. extractionextracted with EtOAc (3×20 mL)
3. washThe combined organics were washed with water (2×15 mL), brine (20 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated
7. customthe residue was purified by flash column chromatography

ORDレコード

ord-384b07a5e64f4767b0c751266be16015

出典データセット

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08957073B2