Triethylamine → HCID 10196037, compound

Participants

Reaction Steps

Combine 3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (0.583 g, 0.968 mmol), 3,4-dimethoxybenzeneboronic acid (0.353 g, 1.94 mmol), copper (II) acetate (0.176 g, 0.968 mmol), triethylamine (0.27 mL, 1.94 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 70% dichloromethane in hexanes and concentrate. Dissolve the resulting compound (0.399 g, 0.511 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0M) in THF (1.35 mL). Stir for 1 h. Add saturated aqueous ammonium chloride(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 a gradient from 25% to 50% ethyl acetate in hexanes to give 0.153 g (31%) of the title compound: mass spectrum (ion spray): m/z=510(M+1); 1H NMR(DMSO-d6): δ8.23 (s, 2H), 7.31 (d, 1H), 7.21 (td, 1H), 7.11-7.06 (m, 2H), 6.94-6.89 (m, 2H), 6.76-6.74 (m, 5H), 3.80 (s, 3H), 3.75 (s, 3H), 2.07 (s, 12H).

Provenance & Evidence