Hexane → 1429329-63-4

A solution 4-iodopyridine (1 g, 4.88 mmol) in THF (15 mL) was cooled to −78° C. under nitrogen, 1.6 M n-BuLi in hexane (0.565 mL, 8.14 mmol) was slowly added at −78° C. The reaction mixture was stirred for 10 min and 1-(2-(4-fluorophenyl)thiazol-5-yl) ethanone (900 mg, 4.07 mmol) in THF (25 mL) was added. The resulting mixture was stirred at −78° C. for 2 h. The reaction mixture was quenched with saturated NH4Cl solution (160 mL), extracted with ethyl acetate (3×250 mL), the organic layer dried over Na2SO4, filtered and concentrated under reduced pressure to obtain crude product. The crude product was purified by flash chromatography (100-200μ; 70% ethyl acetate in hexane) to afford 1-(2-(4-fluorophenyl)thiazol-5-yl)-1-(pyridin-4-yl)ethanol as off-white solid (1.2 g, 35% yield) in 99.6% HPLC purity. 1H NMR (400 MHz, DMSO-d6): δ 8.51 (d, 2H), 7.88-7.92 (m, 2H), 7.81 (s, 1H), 7.48 (d, 2H), 7.28 (t, 2H), 6.64 (s, 1H), 1.93 (s, 3H); LC-MS m/z calculated for [M+H]+301.07. found 301.1.

1. stirringThe resulting mixture was stirred at −78° C. for 2 h
2. customThe reaction mixture was quenched with saturated NH4Cl solution (160 mL)
3. extractionextracted with ethyl acetate (3×250 mL)
4. dry with materialthe organic layer dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customto obtain crude product
8. customThe crude product was purified by flash chromatography (100-200μ; 70% ethyl acetate in hexane)

ORD record

ord-cde37443ce9b42cdb3d28c0253fd4db3

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371316B2