Hydrochloric Acid → HCID 67110273, compound

Participants

Reaction Steps

A mixture of 4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (300 mg, 0.85 mmol) (prepared according to WO 2004108681) and bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate (1.09 g, 2.12 mmol) in CH2Cl2 (10 mL) was stirred at r.t. for 16 h, then diluted with CH2Cl2 (50 mL). The resulting mixture was washed with 5% sodium thiosulfate and 1 M HCl. The organic layer was dried over MgSO4 and concentrated. To the residue were added CuCN (152 mg, 1.70 mmol) and anhydrous DMF (10 mL), and the resulting mixture was refluxed for 20 min. The reaction mixture was poured into a mixture of CH2Cl2 and water. 4 M HCl was added with vigorous stirring until no solid was observed. The aqueous layer was extracted with additional CH2Cl2, and the organic layers were combined, dried over MgSO4 and concentrated. The crude product was purified by column chromatography (0-30% EtOAc/hexanes) to give 274 mg of the title compound as a white solid. MS: (+) m/z 379.09 (M+1).

Provenance & Evidence