Triethylamine → HCID 10310500, compound

Participants

Reaction Steps

Combine 3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (0.700 g, 1.16 mmol), pyridine-4-boronic acid (0.286 g, 2.33 mmol), copper (II) acetate (0.211 g, 1.16 mmol), triethylamine (0.33 mL, 2.33 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 10% ethyl acetate in hexanes. Dissolve the resulting compound (0.103 g, 0.152 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0 M) in THF (0.40 mL). Stir for 1 h. Add saturated aqueous ammonium chloride(10 mL), water (40 mL)m and ethyl acetate (50 mL). Separate the layers and concentrate the organic layer in vacuo. Chromatograph on silica gel eluting with a gradient from 50% to 75% ethyl acetate in hexanes to give 0.109 g (21%) of the title compound: mass spectrum (ion spray): m/z=451(M+1); 1H NMR(DMSO-d6): δ8.46 (dd, 2H), 8.27 (s, 2H), 7.59 (dd, 2H), 7.34 (d, 1H), 7.29 (t, 1H), 7.16 (t, 1H), 7.06(d, 1H), 6.73 (s, 4H), 2.06(s, 12H).

Provenance & Evidence