1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine → 1,4-Dimethyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1H-pyrazole-3-carboxamide

Participants

Reaction Steps

1,4-Dimethyl-1H-pyrazole-3-carbonyl chloride (46 mg) in DCM (2.5 ml) was added over 5 min to 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (100 mg) in DCM (2.5 ml) and pyridine (0.023 ml). The reaction was stirred at room temperature for 2 h. Separately, 1,4-dimethyl-1H-pyrazole-3-carbonyl chloride (273 mg) in DCM (5 ml) was added over 10 min to 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (600 mg) in DCM (25 ml) and pyridine (0.2 ml). The reaction was stirred at room temperature for 1 h. The reactions were combined and separated between saturated sodium bicarbonate (aq) and DCM. The DCM was passed through a hydrophobic frit then dried. The residue was dissolved in DCM and purified using a silica cartridge, preconditioned with cyclohexane. The cartridge was eluted with cyclohexane:diethyl ether (1:1, v/v) then diethyl ether, then 10% methanol in diethyl ether and finally with 50% methanol in diethyl ether. Pure fractions were combined and dried to give title compound, 753 mg.

Provenance & Evidence