Dimethylformamide → HCID 1207821, compound

Participants

Reaction Conditions

Reaction Steps

2-methyl-5-nitro-1H-indole-3-carbonitrile (200 mg, 0.98 mmol) was dissolved in DMF (4 mL) followed by the addition of N,N-dimethylformamide dimethyl acetal (452 mg, 505 μL, 3.8 mmol). The mixture was heated at 80° C. for 0.5 h and turned from amber-colored to dark red over the course of the reaction. The solvent was removed in vacuo and the crude solid was washed with 5:1 EtOAc/hexane (6×10 mL), followed by hexane (2×10 mL) to obtain 2-((E)-2-(dimethylamino)vinyl)-1-methyl-5-nitro-1H-indole-3-carbonitrile as a dark burgundy solid (235 mg, 89% yield) after drying. Mass and purity were confirmed by LC/MS using an acetonitrile gradient with 5 mM ammonium formate pH 6.5. Theoretical (M+H)+ m/z for C14H14N4O2=271.11; Found 271.07. 1H NMR (400 mHz, DMSO-d6) δ 8.12 (d, J=2.2 Hz, 1H), 7.99 (dd, J=9.0, 2.3 Hz, 1H), 7.72 (d, J=13.3 Hz, 1H), 7.61 (d, J=9.0 Hz, 1H), 5.17 (d, J=13.3 Hz, 1H), 3.73 (s, 3H), 3.00 (s, 6H).

Provenance & Evidence