Hydrochloric Acid → HCID 57968770, compound

Participants

Reaction Steps

To a clear solution of 2-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-6-(2-methoxy-ethylamino)-nicotinonitrile (10) (440 mg, 1.04 mmol) in MeOH (anhydrous, 100 mL) was slowly added NaBH4 (120 mg, 3.12 mmol). The reaction was stirred at room temperature for 4 hours, before the addition of HCl solution (1 M, 50 mL). The stirring was kept at room temperature overnight. Then the solution was slowly concentrated in vacuo. Purification was accomplished by preparative HPLC to afford the title compound (108 mg, 32% yield) as a white lyophilizate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.23 (br. s., 1H), 7.86 (br. s., 1H), 7.79-7.68 (m, 2H), 7.24 (s, 1H), 7.18-7.13 (m, 1H), 6.30 (d, J=8.6 Hz, 1H), 4.98 (s, 2H), 3.20 (d, J=1.6 Hz, 2H), 3.17-3.06 (m, 5H); ES-MS m/z=326 (M+H)+; HPLC: 99.39% (220 nm), 99.24% (MaxPlot).

Provenance & Evidence