Sodium Carbonate → HCID 86761319, compound

Participants

Reaction Steps

1-Chloroisoquinolin-7-yl boronic acid (0.55 g, 2.67 mmol), 4-(trifluoromethanesulfonyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.68 g, 2.05 mmol), lithium chloride (0.26 g, 6.16 mmol), 2M aqueous sodium carbonate (2.9 ml, 5.8 mmol) and acetonitrile (15 mL) were combined under nitrogen, and palladium tetrakistriphenylphosphine (0.12 g, 0.103 mmol) added. The reaction mixture was refluxed for 90 minutes, cooled to room temperature, and concentrated in vacuo to give a wet solid. Ammonium hydroxide (3 mL of 30% aqueous solution) was added, and the material partitioned between methylene chloride (150 mL) and 2M aqueous sodium carbonate (25 mL). The organic phase was separated, and the aqueous extracted successively with methylene chloride. The combined organic extracts were dried over magnesium sulfate, and purified by flash column chromatography on silica gel to give the product as a white solid (0.43 g, 1.25 mmol). 1H NMR (CDCl3) δ 8.26-8.20 (m, 2H), 7.88-7.75 (m, 2H), 7.57 (d, 1H), 6.28 (br s, 1H), 4.20-4.12 (m, 2H), 3.76-3.66 (m, 2H), 2.75-2.62 (m, 2H), 1.56 (s, 9H). ESI MS (M+1)+: 259, 261 (Cl).

Provenance & Evidence