Dimethyl-1,3-thiazole-5-carboxylic acid → 2-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-4-methyl-thiazole-5-carboxylic acid

To a stirred solution of 2,4-dimethyl-thiazole-5-carboxylic acid (650 mg, 7.0 mmol) in THF (33 mL) at −70° C. and under argon was added BuLi (1.6M in hexanes, 4.94 mL, 7.9 mmol) dropwise. After 2 h a solution of 3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehyde (814 mg, 3.95 mmol) in THF (12 mL) was added dropwise. After 2 h the reaction mixture was quenched with citric acid solution (5%, 25 mL) then warmed to room temperature and extracted with ethyl acetate. The combined extracts were washed with brine, water, dried over sodium sulfate, filtered and concentrated. Purification by recrystallization (ethyl acetate) afforded the title compound (729 mg, 51%) as a light yellow solid. MS: m/e=362.2 [M+H]+.

1. customAfter 2 h the reaction mixture was quenched with citric acid solution (5%, 25 mL)
2. extractionextracted with ethyl acetate
3. washThe combined extracts were washed with brine, water
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customPurification
8. customby recrystallization (ethyl acetate)

ORD 기록

ord-07c00ccfa2b840d5a9a28440a16892b1

출처 데이터셋

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08178522B2