Hydrochloric Acid → HCID 10288345, compound

Participants

Reaction Steps

Combine 3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (0.622 g, 1.03 mmol), pyridine-3-boronic acid (0.254 g, 2.07 mmol), copper (II) acetate (0.187 g, 1.03 mmol), triethylamine (0.29 mL, 2.07 mmol), 4 angstrom molecular sieves, and dichloromethane (15 mL). Stir at room temperature overnight under ambient atmosphere. Filter the reaction through Celite. Elute through a column of silica gel with 50% dichloromethane in hexanes. Dissolve the resulting compound (0.103 g, 0.152 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0M) in THF (0.40 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 0.036 g (8%) of the title compound: mass spectrum (ion spray): m/z=451 (M+1); 1H NMR(DMSO-d6): δ8.70 (d, 1H), 8.65 (dd, 1H), 8.25 (s, 2H), 7.98-7.94 (m, 1H), 7.62-7.59 (m, 1H), 7.34 (d, 1H), 7.25 (td, 1H), 7.14 (td, 1H), 6.84 (d, 1H), 6.75 (s, 4H), 2.07 (s, 12H).

Provenance & Evidence