Hexane → HCID 71544349, compound

Temperature

-78 °C

To a solution of 4-iodo pyridine (0.142 g, 0.635 mmol) in THF (12 mL) at −78° C. was added n-BuLi in hexane (1.6 M, 0.582 mL, 0.8474 mmol) and the mixture stirred for 30 min A solution of 1-(5-(4-fluorophenyl)-1,3,4-thiadiazole-2-yl)propan-1-one (0.1 g, 0.4237 mmol) in THF (8 mL) was added to above solution at −78° C. and the mixture stirred for 1 hour at −78° C. The reaction mixture was quenched with saturated ammonium chloride solution (20 mL) and diluted with water (25 mL). The reaction mixture was extracted with ethyl acetate (200 mL), dried over sodium sulfate and concentrated under reduced pressure to obtain crude product. The crude compound was purified by preparative TLC (using 5% methanol and dichloromethane) to afford 1-(5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl)-1-(pyridin-4-yl)propan-1-ol as white solid (22 mg, 17% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.55 (d, 2H), 8.0-7.96 (m, 2H), 7.56 (d, 2H), 7.35 (t, 2H), 7.06 (s, 1H), 2.40-2.30 (m, 2H), 0.80 (t, 3H); LC-MS m/z calculated for [M+H]+ 316.08. found 316.1.

1. additionwas added to above solution at −78° C.
2. customThe reaction mixture was quenched with saturated ammonium chloride solution (20 mL)
3. additiondiluted with water (25 mL)
4. extractionThe reaction mixture was extracted with ethyl acetate (200 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customto obtain crude product
8. customThe crude compound was purified by preparative TLC (using 5% methanol and dichloromethane)

ORD record

ord-f221664e05f644278653ccf2a45e8b9b

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266873B2