Citric Acid → HCID 86687476, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial charged with 5-(2-fluoro-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)naphthalene-2-sulfonamide (0.111 g, 0.248 mmol), 1H-imidazole (0.051 g, 0.744 mmol), 1 mL dioxane, and lithium tert-butoxide (1N in THF) (0.992 ml, 0.992 mmol) was heated to 180° C. in the microwave for 90 minutes. LC/MS showed incomplete reaction, so the reaction mixture was heated to 180° C. for an additional 90 minutes. LC/MS showed mostly product, so the reaction mixture was poured into 1N citric acid solution and was extracted with EtOAc. The organics were concentrated. Purification of the crude residue by reverse phase column chromatography [10 to 100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] gave 5-(2-(1H-imidazol-1-yl)-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)naphthalene-2-sulfonamide (0.060 g, 0.121 mmol, 48.8% yield). 1H NMR (DMSO-d6) δ ppm: 8.57 (s, 1H), 8.54 (s, 1H), 8.20 (d, J=8.3 Hz, 1H), 7.95-8.04 (m, 2H), 7.70-7.80 (m, 2H), 7.62-7.68 (m, 1H), 7.56-7.62 (m, 1H), 7.53 (d, J=9.0 Hz, 1H), 7.48 (s, 1H), 6.98 (d, J=6.3 Hz, 1H), 6.94 (s, 1H), 6.60 (s, 1H). m/z (ESI) 496.0 (M+H)+

Provenance & Evidence