Sodium Chlorite → HCID 178480355, compound

Participants

Reaction Conditions

Reaction Steps

To 750 mg (1.6 mmol) of 8-[4-[(Cis)-4-(5-cyano-1-methyl-1H-indole-3-yl)cyclohexyl]-1-piperazinyl]-6-quinolinecarbaldehyde in 60 mL of t-BuOH and 8 mL of CH3CHC(CH3)2 at 23° C. was added a solution of 1.3 mg (14.4 mmol) NaClO2, 1.3 g (10.8 mmol) NaH2PO4 in 3 ml water. After stirring at 23° C. for 12 hours, the volatiles were removed by rotary evaporation. The reaction mixture was transferred to a separatory funnel and partitioned between water and CH2Cl2. The organics were washed with brine, dried over MsSO4, and chromatographed on silica gel eluting with 20:1 CH2Cl2:MeOH containing 5% glacial HOAc. The product fractions were pooled, stripped, and treated with 75 mg (0.83 mmol) of (CO2H)2 in absolute EtOH to give 390 mg (0.6 mmol, a 38% yield) of the oxalate salt of the title compound as a tan crystalline solid. mp: 230° C.; MS (ES) m/z: 494 (MH)+.

Provenance & Evidence