Methanol → HCID 10150867, compound

Participants

Reaction Steps

A mixture of N-(6,7-Methylenedioxycinnolin-4-yl)-N-(n-butyl)-2-iodo-4,5-dimethoxybenzamide (1.0 mmol equiv.), Pd(OAc)2 (0.2 mmol equiv.), P(o-tolyl)3 (0.4 mmol equiv.), and Ag2CO3 (2.0 mmol equiv) was heated to reflux in DMF (30 mL per mmol equiv.) with stirring. The reaction mixture was allowed to cool to room temperature, diluted with CHCl3, and filtered through Celite. The sicciate was extensively washed with 10% CH3OH in CHCl3. The filtrate was concentrated in vacuo and the residue chromatographed on silica gel using chloroform:methanol to provide the title compound (123 mg, 0.2 mmol) in 27% yield with a reaction time 90 min; mp 299° C.; IR (KBr) 1654; 1H NMR (CDCl3) δ 1.06 (t, 3H, J=7.4), 1.56 (m, 2H), 2.13 (m, 2H), 4.09 (s, 3H), 4.17 (s, 3H), 4.49 (m, 2H), 6.26 (s, 2H), 7.62 (s, 1H), 7.85 (s, 1H), 7.87 (s, 1H), 8.65 (s, 1H); 13C NMR (CDCl3) δ 13.8, 20.2, 31.1, 48.6, 56.3, 56.6, 98.8, 102.7, 104.2, 106.5, 107.9, 119.7, 149.1, 150.1, 150.9, 151.4, 153.6, 154.2, 162.9; HRMS calcd for C22H21N3O5H: 408.1559. Found 408.1543.

Provenance & Evidence