Potassium Phosphate, Tribasic → Methyl 4-cyano-3-(4-isoquinolinyl)benzoate

Participants

Reaction Conditions

Reaction Steps

The mixture of 4-cyano-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (100 mg, 0.348 mmole), 4-bromo-isoquinoline (80 mg, 0.383 mmole), Pd2(dba)3 (31.9 mg, 0.035 mmole), Sphos (28.6 mg, 0.070 mmole), 2 molar K3PO4 aqueous (0.4 ml, 0.8 mmole) and dioxane (5 ml) was degassed and heated to 120° C. for 40 minutes in microwave. Reaction solution was diluted with water and extracted with EtOAc. EtOAc layer was concentrated. Residue was purified by using silica gel chromatography, eluting with EtOAc/heptane to afford 4-cyano-3-isoquinolin-4-yl-benzoic acid methyl ester (60 mg, 60%). 1H NMR (400 MHz, CD2Cl2) δ 3.88 (s, 3H), 7.45 (d, J=8.03 Hz, 1H), 7.65 (m, 2H), 7.90 (m, 1H), 8.06 (d, J=8.53 Hz, 1H), 8.15 (m, 2H), 8.42 (s, 1H), 9.29 (s, 1H). HR-MS m/z 289.0979 [M+1].

Provenance & Evidence