Sodium Carbonate → HCID 10253960, compound

Participants

Reaction Steps

A mixture of trifluoromethanesulfonic acid 8-chloro-2-(2,4-dimethylbenzyl)-1-oxo-1,2-dihydroisoquinolin-3-yl ester (61.9 mg, 0.14 mmol), 4-phenoxyphenylboronic acid (45.9 mg, 0.21 mmol), and triphenylarsine (17.6 mg, 57.5 μmol) in THF (0.7 mL) under a nitrogen atmosphere was treated with bis-(acetonitrile) palladium (II) chloride (4.6 mg, 17.7 μmol) and aqueous sodium carbonate solution (0.7 mL of a 2 M solution) with vigorous stirring at ambient temperature. After 90 minutes stirring at ambient temperature, TLC analysis showed only a trace of starting trifluoromethanesulfonic acid 8-chloro-2-(2,4-dimethylbenzyl)-1-oxo-1,2-dihydroisoquinolin-3-yl ester remaining. The reaction was diluted with ether (20 mL), and water (10 mL). The basic aqueous layer was extracted with ether (3×10 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and conc. to afford a yellow semi-solid. The material was purified by silica gel column chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane. The main peak was collected to afford 8-chloro-2-(2,4-dimethylbenzyl)-3-(4-phenoxyphenyl)-2H-isoquinolin-1-one (41 mg, 63% yield) as a brittle white foam contaminated with a small amount (<10%) of an impurity: 1H-NMR (400 MHz, CDCl3): δ 7.51-7.49 (2H, m), 7.41-7.34 (3H, m), 7.18-7.11 (3H, m),7.04-7.00 (2H, m), 6.94-6.84 (5H, m), 6.68 (1H, d, J=7.8 Hz), 6.42 (1H, s), 5.09 (2H, s), 2.24 (3H, s), 2.00 (3H, s) ppm.

Provenance & Evidence