Diethyl Ether → HCID 86680489, compound

Temperature

0 °C

A solution of 2-(1H-pyrazol-4-yl)thiazole-5-carbaldehyde (245 mg, 1.3 mmol) in THF (15 mL) was cooled to 0° C., a 3M solution of ethyl magnesium bromide in diethyl ether (0.9 mL, 2.7 mmol) slowly added at 0° C., and the reaction mixture stirred for 2 hours at 0° C. The reaction mixture was quenched with saturated NH4Cl solution (10 mL) and extracted with ethyl acetate (2×200 mL). The combined extracts were washed with brine solution (20 mL), dried over Na2SO4, filtered and the organic solvent was concentrated under reduced pressure to obtain crude product. The crude product was purified by flash chromatography (60-120μ; 3% methanol in dichloromethane) to afford 1-(2-(1H-pyrazol-4-yl)thiazol-5-yl)propan-1-ol as pale yellow liquid (180 mg, 63% yield). 1H NMR (400 MHz, DMSO-d6): δ 13.19 (br s, 1H), 8.25 (s, 1H), 7.88 (s, 1H), 7.51 (s, 1H), 5.59 (d, 1H), 4.71 (q, 1H), 1.97-1.64 (m, 2H), 0.86 (t, 3H); LC-MS m/z calculated for [M+H]+210.06. found 210.1.

1. customThe reaction mixture was quenched with saturated NH4Cl solution (10 mL)
2. extractionextracted with ethyl acetate (2×200 mL)
3. washThe combined extracts were washed with brine solution (20 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationthe organic solvent was concentrated under reduced pressure
7. customto obtain crude product
8. customThe crude product was purified by flash chromatography (60-120μ; 3% methanol in dichloromethane)

ORD record

ord-f158f96c183d427d984fad38d5ac3f1d

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371316B2