Ethyl Acetate → HCID 66899702, compound

Participants

Reaction Conditions

Reaction Steps

To methyl 5-bromo-1-(2,2-dimethoxyethyl)-1H-indazole-7-carboxylate from Step D of Example 10 in DMF (100 mL) was added potassium carbonate (622 mg, 4.5 mmol), tetrakis(triphenylphosphine)palladium(0) (347 mg, 0.3 mmol) and trimethylboroxine (377 mg, 3.0 mmol) and the reaction mixture was stirred at 100° C. for 24 h. Then another portion of trimethylboroxine (377 mg, 3 mmol) was added and the reaction was further stirred for 6 h. Ethyl acetate was added and the reaction was washed with water and concentrated in vacuo. The crude mixture was purified by column chromatography (silica gel, 0-30% ethyl acetate/hexanes) to afford methyl 1-(2,2-dimethoxyethyl)-5-methyl-1H-indazole-7-carboxylate (213 mg, 51%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 8.00 (s, 1H), 7.73 (s, 1H), 7.65 (s, 1H), 4.92 (d, J=5.5 Hz, 2H), 4.54 (t, J=5.5 Hz, 1H), 3.98 (s, 3H), 3.28 (s, 6H), 2.47 (s, 3H); MS (ESI+) m/z 279 (M+H).

Provenance & Evidence