Citric Acid → 3-(3-Aminoisoquinolin-7-yl)-4-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-bromoisoquinolin-3-amine (299.9 mg; 1.344 mmol), 4-methyl-3-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (387.1 mg; 1.560 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (51.5 mg; 0.0727 mmol), potassium carbonate (569.3 mg; 4.119 mmol), dioxane (10 mL) and water (1 mL) was stirred at 90° C. for 24 hours and then cooled to room temperature. The reaction mixture was acidified with 10% aqueous citric acid (10 mL). The product was recovered as a red-brown precipitate via filtration, rinsed with water and ethyl acetate, and dried under vacuum to yield 253.4 mg (68%) of the title compound which was carried forward without additional purification. LCMS (ESI): M+H=279.2; 1H NMR (400 MHz, DMSO) δ 8.87 (s, 1H), 7.84 (d, J=7.9 Hz, 1H), 7.81 (d, J=13.1 Hz, 2H), 7.59 (d, J=8.6 Hz, 1H), 7.46 (t, J=9.5 Hz, 2H), 6.67 (s, 1H), 5.96 (s, 2H), 2.34 (s, 3H).

Provenance & Evidence