Sodium hydride → HCID 16226478, compound

Participants

Reaction Steps

303 mg (0.81 mmol) of compound B 3-(4-fluorophenyl)-1,9-dimethyl-6-(1H-pyrazol-3-yl)-1,9-dihydropyrido[2,3-b]indol-2-one are dissolved in 8 ml of DMF. 50 mg (1.22 mmol) of 60% NaH and a spatula of dibenzo-18-crown-6 are added. After stirring for 5 minutes, 73 μl (0.89 mmol) of bromomethyl methyl ether are added. The mixture is left to stir for 4 h at ambient temperature. A saturated NaHCO3 solution is added, the mixture extracted with EtOAc, and the organic phase is dried over MgSO4, filtered, and concentrated to dryness, adsorbing onto silica. The mixture is enriched in beta isomer by chromatography on a silica column, elution being carried out with 70/30 EtOAc/cyclohexane (ratio obtained: 62/38 beta/alpha) and then by means of a second purification by chromatography on a silica column, elution being carried out with 60/40 EtOAc/cyclohexane.

Provenance & Evidence