Sodium Hydroxide → HCID 59596464, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 3-(2-fluoro-4-iodo-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (100 mg, 0.23 mmol), 1N aqueous sodium hydroxide (0.25 ml) and MeOH (3.0 ml) was heated at 65° C. for 1.5 hours. The reaction mixture was concentrated and azeotroped with toluene (2×2 ml) to give a solid residue. The solid residue was dissolved in anhydrous THF (4 ml) and O-(2-vinyloxy-ethyl)-hydroxylamine (47 mg, 0.46 mmol), EDCI (55 mg, 0.29 mmol), HOBt (43 mg, 0.32 mmol) and DIPEA (119 μl, 0.68 mmol) were added. After stirring for 72 hours at ambient temperature, the mixture was evaporated and the residue was partitioned between ethyl acetate (30 ml) and water (20 ml). The organic layer was isolated, dried over sodium sulphate, then filtered and evaporated to give a yellow oil. The oil was purified by flash chromatography (Si-PPC, dichloromethane:methanol, gradient 100:0 to 90:10) to afford the title compound as a yellow solid (64 mg, 57%). LCMS (method B): RT=2.20 min, M+H+=497.

Provenance & Evidence