Triethylamine → HCID 10152224, compound

Participants

Reaction Steps

Combine 3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (0.350 g, 0.581 mmol), 3isopropylphenylboronic acid (0.190 g, 1.16 mmol), copper (II) acetate (0.106 g, 0.581 mmol), triethylamine (0.16 mL, 1.16 mmol), 4 angstrom molecular sieves, and dichloromethane (10 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 (0.189 g, 0.268 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0 M) in THF (0.67 mL). Stir for 1 h. Add saturated aqueous ammonium chloride(10 mL), water and ethyl acetate (50 mL). Separate the layers and concentrate the organic layer in vacuo. Chromatograph on silica gel eluting with 25% to 50% ethyl acetate in hexanes to give 0.089 g (31%) of the title compound: mass Spectrum (ion spray): m/z=492(M+1); 1H NMR(DMSO-d6); δ8.36 (s, 2H), 7.54 (t, 1H), 7.41-7.37 (m, 2H), 7.32-7.27 (m, 3H), 7.16 (t, 1H), 6.83-6.80 (m, 5H), 3.05-3.01 (m, 1H), 2.13 (s, 12H), 1.28 (d, 6H).

Provenance & Evidence