Sodium Carbonate → HCID 86680610, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromopicolinaldehyde (0.25 g, 1.34 mmol) in toluene (6 mL) and EtOH (5 mL) was added (4-(methylcarbamoyl)phenyl)boronic acid (0.36 g, 2.0 mmol), 2M Na2CO3 (2.5 mL, 4.03 mmol) and Pd(PPh3)4 (0.24 g, 0.2 mmol) under argon. The mixture was degassed, heated to 100° C., and stirred for 1 h. After completion of the reaction by monitoring with TLC (80% EtOAc\hexane), the resulting mixture was filtered using Celite® reagent. The filtrate was separated, 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 column chromatography (silica gel 100-200μ) using 60% ethyl acetate in hexane and isolated as a yellow solid (0.22 g, 62% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.0 (s, 1H), 9.20 (s, 1H), 8.53 (s, 2H), 8.39 (d, 2H), 7.9 (m, 3H); LC-MS: m/z 241.4 [M+H]+.

Provenance & Evidence