Sodium borohydride → HCID 67362707, compound

Participants

Reaction Steps

To a solution of 8 (40 mg, 0.16 mmol) in dry ethanol (5 mL), under argon, was added NaBH4 (9 mg, 0.24 mmol). The solution was stirred at room temperature for 30 min then the solvent was removed in vacuo. An aqueous saturated Na2CO3 solution (5 mL) was added and the solution was extracted with CH2Cl2 (3×20 mL). The organic layers were dried (MgSO4), filtered and evaporated to give compound 11 (23 mg, 57%); mp 227-229° C.; IR (KBr) 3289, 1685, 1266, 1191 cm−1; 1H NMR (400 MHz, DMSO-d6) δ 1.38 (t, 3H, J=7 Hz), 4.38 (q, 2H, J=7 Hz), 4.60 (s, 2H), 5.17 (brs, 1H), 7.01 (d, 1H, J=7 Hz), 7.33 (s, 1H), 7.72 (s, 1H), 8.29 (d, 1H, J=7 Hz), 12.50 (brs, 1H); 13C NMR (100 MHz, DMSO-d6) δ 14.3, 58.0, 60.4, 101.1, 106.4, 110.3, 113.1, 124.4, 125.6, 133.1, 140.2, 144.7, 160.5; MS m/z 259 (M+, 60), 213 (52), 212 (100), 184 (22), 57 (25). Anal. Calcd for C13H13N3O3: C, 60.22; H, 5.05; N, 16.21. Found: C, 60.13; H, 5.18; N, 16.02.

Provenance & Evidence