Potassium Carbonate → HCID 59549920, compound

Participants

Reaction Steps

A mixture of tert-butyl 2-(3-cyano-4fluorophenyl)acetate (0.0825 g, 0.351 mmol), N-(4-chlorophenethyl)-2-methyl-1H-benzo[d]imidazole-5carboxamide (0.100 g, 0.319 mmol) and potassium carbonate (0.0661 g, 0.478 mmol) was stirred together in 3 mL of DMSO at 85° C. After stirring for 4 hours, the reaction was loaded onto a silica gel samplet and the product eluted using a gradient of 5% ethyl acetate/hexanes to 100% ethyl acetate/hexanes. The resulting oil was dissolved in DCM (1 mL) and treated with TFA (1 mL). After 2 hours, the reaction was concentrated, and the residue was loaded onto silica gel. The product was eluted using a gradient of 0.5% MeOH/DCM containing 0.5% AcOH to 10% MeOH/DCM containing 0.5% AcOH to provide 2-(4-(5-(4-chlorophenethylcarbamoyl)-2-methyl-1H-benzo[d]imidazol-1yl)3-cyanophenyl)acetic acid and 2-(4-(6-(4-chlorophenethylcarbamoyl)-2-methyl-1H-benzo[d]imidazol-1-yl)-3-cyanophenyl)acetic acid (0.045 g, 29.9% yield) as a 2:1 mixture. 1H NMR (400 MHz, CD3OD) δ 8.49 (t, J=5.5 Hz, NH), 7.77-7.82 (m, 2H), 7.68 (s, 1H), 7.52-7.54 (m, 1H), 7.20-7.32 (m, 4H) 7.00-7.08 (m, 2H), 3.71 (s, 2H), 3.58 (q, J=6.8 Hz, 2H), 3.30 (s, 3H), 2.90 (t, J=7.3 Hz, 2H). MS(APCI)=473.5 (M+1).

Provenance & Evidence