Sodium Carbonate → HCID 178519821, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromothiazole-5-carbaldehyde (0.8 g, 4.16 mmol) in toluene (6 mL) and EtOH (5 mL), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (1.8 g, 6.2 mmol), 2M Na2CO3 (6.2 mL, 12.4 mmol) and Pd(PPh3)4 (0.45 mg, 0.4 mmol) were added under argon. The mixture was degassed, heated to 100° C., stirred for 1 h. After completion of the reaction, by monitoring with TLC (5% MeOH\DCM), the resulting mixture was filtered with Celite® reagent and the filtrate was separated. This filtrate was concentrated, extracted with EtOAc (2×100 mL), washed with water (100 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by Biotage Isolera® One column purifier (silica gel 100-200 microns) using 3% methanol in dichloromethane and isolated as yellow color solid (0.25 g, 33% yield). 1H NMR (400 MHz, DMSO-d6): δ 13.49 (brs, 1H), 10.03 (s, 1H), 8.60 (s, 1H), 8.55 (s, 1H), 8.09 (s, 1H); LC-MS m/z calcd for [M+H]+, 180.02. found, 180.1.

Provenance & Evidence