Dimethylformamide → HCID 59854617, compound

Participants

Reaction Conditions

Reaction Steps

5-fluoro-2-methyl-1H-indole-3-carbaldehyde (50 mg, 0.28 mmol) was dissolved in 3 mL dry DMF, followed by the addition of N,N-dimethylformamide dimethyl acetal (124 mg, 138 μL, 1.04 mmol). The reaction mixture was heated to 80° C. for 4 h and turned from light yellow to dark red over the course of the reaction. The crude reaction was concentrated in vacuo, dissolved in 0.5 mL DMSO/MeOH, and purified by reverse phase HPLC (5-95% water/acetonitrile gradient over 60 minutes) to obtain 2-((E)-2-(dimethylamino)vinyl)-5-fluoro-1-methyl-1H-indole-3-carbaldehyde as a pale yellow solid (40 mg, 62% yield). 1H NMR (400 mHz, DMSO-d6) δ 9.73 (s, 1H), 7.73 (dd, J=9.8, 2.6 Hz, 1H), 7.39 (m, 2H), 6.96 (dt, J=9.2, 2.6 Hz, 1H), 5.20 (d, J=13.1 Hz, 1H), 3.66 (s, 3H), 2.99 (s, 6H). 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 C14H15FN2O=247.12; Found 247.06.

Provenance & Evidence