Sodium Carbonate → HCID 84819770, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromopicolinaldehyde (0.7 g, 3.76 mmol) in toluene (8 mL) and EtOH (6 mL) was added (4-(hydroxymethyl)phenyl)boronic acid (0.68 g, 4.516 mmol), 2M Na2CO3 (5.6 mL, 11.3 mmol) and Pd(PPh3)4 (0.2 mg, 0.188 mmol) under argon. The mixture was degassed and heated to 100° C. and stirred for 2 h. After completion of the reaction by monitoring with TLC (60% EtOAc\hexane), the resulting mixture was filtered with Celite® reagent and the filtrate was separated. The 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 a Biotage Isolera® One column purifier (silica gel 100-200μ) using 38% ethyl acetate in hexane to provide a yellow solid (0.6 g, 75% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.01 (s, 1H), 9.14 (d, 1H), 8.306 (dd, 1H), 7.98 (d, 1H), 7.80 (d, 2H), 7.47 (d, 2H), 5.25 (s, 1H), 4.56 (d, 2H); LC-MS: m/z 214.3 [M+H]+.

Provenance & Evidence