Stannane, tributyl(1-methylethenyl)- → HCID 57781108, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(5-iodo-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (0.700 g, 1.90 mmol) (Example 2b) in NMP (5 mL) is added tris(dibenzylideneacetone)dipalladium (0.196 g, 0.19 mmol) and trifuryl-2-yl-phospane (0.066 g, 0.285 mmol). Tributylisopropenyltin (1.25 g, 3.80 mmol) is added to the reaction mixture and it is heated to 90° C. for 24 h. The mixture is then allowed to cooled to room temperature, washed with water and extracted with ethyl acetate. The organic phase is dried over Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (dichloromethane-methanol, 19:1) to give 4-(5-isopropenyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a white solid; (ESI) m/z 283.0 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.21 (s, 3 H), 1.50 (s, 3 H), 2.24 (br. s, 3 H), 5.31 (br. s, 1 H), 5.56 (br. s, 1 H), 5.73 (s, 1 H), 7.02 (br. s, 1 H), 7.28 (br. s, 1 H), 7.51 (d, J=7.8 Hz, 1 H), 7.69 (td, J=7.8, 1.0 Hz, 1 H), 7.81 (td, J=7.6, 1.3 Hz, 1 H), 8.25 (d, J=7.8 Hz, 1 H).

Provenance & Evidence