Sodium Carbonate → Methyl 7-(4-hydroxyphenyl)-3-isoquinolinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A suspension of 700 mg (2.09 mmol) of methyl 7-{[(trifluoromethyl)sulfonyl]oxy}-3-isoquinolinecarboxylate, 715 mg (3.13 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 240 mg (0.21 mmol) of tetrakistriphenylphosphine palladium(0) and 3.70 mL (3.31 mmol) of 2.0 M Na2CO3 (aq) in 10 mL of 1,2-dimethoxyethane was stirred at 90° C. for 20 min. The suspension was filtered through a pad of Celite® and the filter cake was washed with EtOAc. The combined organics were then evaporated and the residue purified by silica gel chromatography (40 g of silica gel eluting with 0-15% acetone in CH2Cl2 over 45 minutes) to give 360 mg (62%) of methyl 7-(4-hydroxyphenyl)-3-isoquinolinecarboxylate as a beige solid. 1H NMR (400 MHz, DMSO-d6): δ 9.75 (s, 1H), 9.38 (s, 1H), 8.42 (s, 1H), 8.23 (s, 1H), 8.21 (d, J=8 Hz, 1H), 8.15 (d, J=8 Hz, 1H), 7.72 (d, J=9 Hz, 2H), 6.91 (d, J=9 Hz, 2H), 3.91 (s, 3H). ESI-LCMS m/z 280 (M+H)+.

Provenance & Evidence