Dimethylformamide → HCID 86758916, compound

Participants

Reaction Steps

POCl3 (16.37 g, 106.76 mmol) was slowly added to DMF (225 mL) at 0° C. The mixture was stirred for 15 minutes and then treated with a solution of 3,4-dihydro-2H-[1,4]diazepino[6,7,1-hi]indol-1-one (Example 42, 1.46 g, 7.85 mmol) in DMF (10 mL). The reaction mixture was warmed to rt and stirred for 17 h. After removing all solvent, the residue was taken up in H2O, made basic (pH 12-14) using 50% aqueous NaOH and extracted with EtOAc several times. The organic layer was dried over anhydrous MgSO4, filtered and concentrated to give 1.6 g (95%) of a pale-yellow solid: 1H NMR (DMSO-d6) δ 3.58-3.61 (m, 2H), 4.48 (bs, 2H), 7.37 (t, 1H, J=7.5 Hz), 7.97 (d, 1H, J=7.5 Hz), 8.33-8.35 (m, 2H), 8.43-8.45 (m, 1H), 9.95 (s, 1H). HRMS calcd. for C12H10N2O2 (M+) 214.0742, found 214.0737. Anal. (Cl2H10N2O2.0.1H2O) C, H, N.

Provenance & Evidence