Diethyl Ether → HCID 86680603, compound

Temperature

0 °C

To a solution of 2-(1-methyl-1H-pyrazol-3-yl)thiazole-5-carbaldehyde (0.1 g, 0.51 mmol) in THF (10 mL) at 0° C. was slowly added 3.0 M ethyl magnesium bromide in diethyl ether (0.5 mL, 0.15 mmol), and the reaction mixture was stirred at 0° C. for 3 h. After completion of reaction by monitoring with TLC (5% MeOH\DCM), the reaction mixture was quenched with sat'd. NH4Cl (50 mL) solution. The reaction mixture was then extracted with EtOAc (3×50 mL), washed with water (2×50 mL), dried over Na2SO4 and concentration in vacuo and to provide a yellow solid (0.09 g, 81% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.21 (s, 1H), 7.82 (s, 1H), 7.50 (s, 1H), 5.60 (d, 1H), 4.70 (q, 1H), 3.86 (s, 3H), 1.69 (m, 2H), 0.844 (t, 3H).

1. customat 0° C.
2. customAfter completion of reaction
3. customthe reaction mixture was quenched with sat'd
4. extractionThe reaction mixture was then extracted with EtOAc (3×50 mL)
5. washwashed with water (2×50 mL)
6. dry with materialdried over Na2SO4 and concentration in vacuo

ORD record

ord-cc5c9073890441f9ac0ea59063087062

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199975B2