Sodium Methoxide → HCID 178493218, compound

Participants

Reaction Steps

To an ice-bath cooled suspension of cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (400 mg, 1.174 mmol) in THF (2.3 mL) was added sodium methoxide (25 wt. % in MeOH (0.859 mL, 3.76 mmol)). The mixture was stirred in an ice bath for 1 minute. The ice bath was removed and the reaction was stirred for 30 minutes. The mixture was diluted with 10% IPA/DCM (5 mL) and washed with saturated aqueous NaHCO3 (1 mL). The layers were separated, and the organic layer was dried with Na2SO4 and the mixture purified via flash chromatography using a linear gradient of 0% to 5% of 1% NH4OH in MeOH in DCM. The title compound was collected as a yellow solid (289 mg, 73%).

Provenance & Evidence