Hydrochloric Acid → HCID 57969026, compound

Participants

Reaction Steps

To a clear solution of 6-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-2-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-nicotinonitrile (11) (485 mg, 0.903 mmol) in MeOH (anhydrous, 100 mL) was slowly added NaBH4 (101 mg, 2.65 mmol). The reaction was stirred at room temperature for 4 hours, before the addition of HCl solution (1 M, 60 mL). The stirring was kept at room temperature overnight. Then the solution was slowly evaporated in vacuo. Purification was accomplished by reverse phase Biotage with 10%-100% MeOH/H2O gradient to afford 51 mg (13.8% yield) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.22 (s, 1 H), 7.92 (d, J=8.6 Hz, 1 H), 7.75 (d, J=8.2 Hz, 1 H), 7.24 (s, 1 H), 7.16 (dd, J=7.8, 2.0 Hz, 1 H), 6.43 (br. s., 1 H), 4.98 (s, 2 H), 3.90 (br. s., 1 H), 3.47 (br. s., 2 H), 3.39 (s, 2H, masked), 2.95 (br. s., 3 H); HPLC: 98.18% (220 nm), 99.15% (254 nm), 99.16 (MaxPlot).

Provenance & Evidence