Sodium Carbonate → 3-(pyridin-3-yl)-1H-indazole-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-iodo-1H-indazole-6-carbaldehyde (50 mg, 0.18 mmol), pyridin-3-ylboronic acid (27 mg, 0.22 mmol), PdCl2(PPh3)2 (13 mg, 0.018 mmol) and 2M Na2CO3 (0.10 mL, 0.18 mmol) in DME/H2O/EtOH (1.4 mL/0.4 mL/0.2 mL) was degassed by evacuation and refilling with Ar. The reaction mixture was sealed and heated with stirring under microwave irradiation at 125° C. for 60 min. The crude reaction mixture was concentrated under reduced pressure. Ethyl acetate (5 mL) was added and the solution was washed with brine (2×20 mL), dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel using MeOH (5%) in DCM as the eluent to provide the title compound a pale yellow solid (24 mg, 59%). 1H NMR (400 MHz, CDCl3) δ ppm 10.17 (s, 1H), 8.88 (d, J=2.3 Hz, 1H), 8.69 (d, J=4.8 Hz, 1H), 8.16 (d, J=8.5 Hz, 1H), 8.10 (s, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.82 (d, J=8.5 Hz, 1H), 7.45 (dd, J=8.0, 5.0 Hz, 1H); MS ESI 224.0 (100) [M+H]+, calcd for [C13H9N3O+H]+ 224.07.

Provenance & Evidence