Hydrochloric Acid → HCID 77230773, compound

Participants

Reaction Steps

A solution of 2 M HCl in dioxane (0.47 mL, 0.94 mmol) was added to a stirred, room temperature mixture of tert-butyl 3-formyl-6-methoxy-1H-indazole-1-carboxylate (50 mg, 0.18 mmol) in dioxane (1 mL) and the mixture was stirred at room temperature for 8 hours. It was concentrated and dried under vacuum. To the residue in DMF (1.0 mL), DBU (0.08 mL, 0.54 mmol) was added and the reaction mixture was stirred for 30 minutes. Then 1-iodopropane (0.09 mL, 0.90 mmol) was added and the solution was stirred for 16 hours at room temperature. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate (5 mL), washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (25 mg, 63% crude yield).

Provenance & Evidence