4-Acetylpyridine → HCID 71544125, compound

To a solution of 5-(4-fluorophenyl)thiazole (0.1 g, 0.558 mmol) in dry THF (8 mL) at −78° C., was slowly added n-1.6 M BuLi in hexanes (0.7 mL, 1.117 mmol), the reaction mixture was stirred for 30 minutes and 1-(pyridin-4-yl)ethanone (0.13 mL, 1.117 mmol) in THF (8 mL) was added. The reaction mixture was stirred for 2 hours at −78° C., the reaction mixture quenched with saturated NH4Cl solution (50 mL), extracted with EtOAc (2×50 mL), the organic layer washed with water (50 mL), dried over Na2SO4 and concentrated under reduced pressure to obtain crude product. The crude product was purified by preparative TLC (5% methanol in dichloromethane) to give 1-(5-(4-fluorophenyl) thiazol-2-yl)-1-(pyridin-4-yl)ethanol as off-white solid (35 mg, 22% yield) in 99.6% HPLC purity. 1H NMR (400 MHz, DMSO-d6): δ 8.50 (br s, 1H), 8.03 (s, 1H), 7.66-7.63 (m, 2H), 7.53 (br s, 2H), 7.24 (t, 2H), 6.99 (s, 1H), 1.89 (s, 3H); LC-MS m/z calculated for [M+H]+ 301.07, found 301.4.

1. stirringThe reaction mixture was stirred for 2 hours at −78° C.
2. customthe reaction mixture quenched with saturated NH4Cl solution (50 mL)
3. extractionextracted with EtOAc (2×50 mL)
4. washthe organic layer washed with water (50 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. customto obtain crude product
8. customThe crude product was purified by preparative TLC (5% methanol in dichloromethane)

ORD record

ord-23883e12f1854f8185641aa08dfb2c28

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809372B2