Sodium Carbonate → HCID 86651964, compound

Participants

Reaction Steps

A mixture of 1H-indazole-6-carbaldehyde (50 mg, 0.18 mmol), thiophen-2-ylboronic acid (47 mg, 0.37 mmol), Pd(PPh3)4 (21 mg, 0.018 mmol) and 2M Na2CO3 (0.28 mL, 0.55 mmol) in DME/H2O (2 mL/1 mL) was heated under reflux for 16 hours. The crude reaction mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel using EtOAc (10 to 20%) in DCM as the eluent to provide the title compound as a pale yellow solid (29 mg, 70%). 1H NMR (400 MHz, CD3OD) δ ppm 10.09 (s, 1H), 8.15 (d, J=8.5 Hz, 1H), 8.09 (s, 1H), 7.72 (d, J=8.5 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 7.48 (d, J=5.0 Hz, 1H), 7.19 (dd, J=4.8, 3.8 Hz, 1H); MS ESI 229.0 (100) [M+H]+, calcd for [C12H8N2OS+H]+ 229.04.

Provenance & Evidence