Hydrochloric Acid → HCID 10310991, compound

Participants

Reaction Steps

Combine 3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (0.680 g, 1.13 mmol), 3-methoxyphenylboronic acid (0.343 g, 2.26 mmol), copper (II) acetate (0.205 g, 1.13 mmol), triethylamine (0.32 mL, 2.26 mmol), 4 angstrom molecular sieves, and dichloromethane (15 mL). Stir at room temperature overnight under ambient atmosphere. Filter the reaction through Celite, and elute through a column of silica gel with 70% dichloromethane in hexanes and concentrate. Dissolve the resulting compound (0.417 g, 0.589 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0 M) in THF (1.47 mL). Stir for 1 h. Add 1N aqueous HCl(10 mL), water (40 mL), and ethyl acetate (50 mL). Separate the layers and concentrate the organic layer in vacuo. Chromatograph on silica gel eluting with ethyl acetate to give 0.155 g (29%) of the title compound: mass spectrum (FAB): m/z=480(M+1); 1H NMR(DMSO-d6): δ8.23 (s, 2H), 7.46 (t, 1H), 7.31 (d, 1H), 7.23 (td, 1H), 7.10 (td, 1H), 7.05-7.02 (m, 1H), 6.98-6.95 (m, 2H), 6.81 (d, 1H), 6.73 (s, 4H), 3.79 (s, 3H), 2.07 (s, 12H).

Provenance & Evidence