Tris(furan-2-yl)phosphane → HCID 24802856, compound

Participants

Reaction Conditions

Reaction Steps

To a flask charged with 4-(5-iodo-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (350 mg, 0.95 mmol) (Example 2b), tris(dibenzylideneacetone)dipalladium(0) (98 mg, 0.095 mmol) and trifuran-2-yl-phosphane (33 mg, 0.142 mmol) and flushed with N2 is added tributylcyclopropyltin (1.89 g, 5.7 mmol) in degassed N-methylpyrrolidinone (3 mL). The mixture is degassed for 15 min and heated to 95° C. for 25 h. The reaction mixture is quenched with water and extracted with ethyl acetate three times. The organic phase is combined, dried over sodium sulfate, concentrated and the residue is purified by semi-preparative reverse phase HPLC to give 4-(5-cyclopropyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as white solid; (ESI) m/z 283.2 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 0.69 (s, 1 H), 0.81 (br. s, 1 H), 1.09 (br. s, 2 H), 1.29 (s, 3 H), 1.56 (s, 3 H), 1.94 (br. s, 1 H), 5.78 (s, 1 H), 6.68 (s, 1 H), 7.14 (br. s, 1 H), 7.42 (d, J=7.1 Hz, 1 H), 7.63 (td, J=7.6, 1.3 Hz, 1 H), 7.75 (td, J=7.6, 1.3 Hz, 1 H), 8.21 (dd, J=7.8, 1.3 Hz, 1 H).

Provenance & Evidence