Diisopropylethylamine → HCID 21868525, compound

Participants

Reaction Steps

211 mg (0.972 mmol) 5-trifluoromethyl-2,4-dichloropyrimidine was taken into 1.00 mL 1:1 tert-butanol:1,2-dichloroethane mixture. To this was added 972 mL (0.972 mmol) zinc chloride solution. 145 mg (0.972 mmol) 5-Amino-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one was taken into 500 mL tert-butanol/1,2-dichloroethane mix with 169 mL (0.972 mmol) diisopropylethylamine and 2.92 mL (2.92 mmol) zinc chloride solution. Allowed both solutions stir at ambient temperature for thirty minutes. The oxindole-bearing solution was slowly added drop-wise to the solution containing the trifluoromethylpyrimidine. Allowed the combined solutions to stir at ambient temperature for sixteen hours. The volatiles from the reaction mixture were removed under reduced pressure. The resulting glass was taken up into 10% methanol in dichloromethane and washed thoroughly with 1 N sodium hydroxide. Organic layer was dried over magnesium sulfate and evaporated under reduced pressure to give a yellow solid. The titled compound was obtained through purification of this yellow solid over silica (97.8:2:0.2 CHCl3:CH3OH:NH4OH) as a yellow solid in a 13% yield (43 mg, 0.130 mmol). APCI m/z 330.0/331.9 (MH+), 1H NMR (D6-DMSO) δ 10.96 (s, 1 H), 10.57 (s, 1 H), 8.74 (s, 1 H), 8.23 (s, 1 H), 7.85 (s, 1 H), 3.56 (s, 2 H) ppm.

Provenance & Evidence