Ethanol → HCID 69248326, compound

Participants

Reaction Steps

Ethyl {1-[4-(tert-butyl)benzyl]-5-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate was prepared from 1-[4-(tert-butyl)benzyl]-5-[4-(trifluoromethoxy)phenyl]-1H-indole (2.52 g, 5.95 mmol), oxalyl chloride (1.6 mL, 18 mmol), and ethanol (5 mL) following the procedure described in Step 3 of Example 1. Purification by reverse phase HPLC using 92% acetonitrile and 8% water as the mobile phase followed by drying for 12 hours at 82° C. yielded the title compound as a light yellow solid (1.84 g, 59%), mp: 141-142° C. Mass spectrum (+ESI, [M+H]+) m/z 524; 1HNMR (500 MHz, DMSO-d6): δ 8.7 (s, 1H), 8.4 (d, 1H J=1.5 Hz), 7.75-8.0 (m, 3H), 7.6 (dd, 1H, J=8.6 Hz and 1.8 Hz), 7.45 (d, 2H, J=8.1 Hz), 7.35 (d, 2H, J=8.4 Hz), 7.25 (d, 2H, J=8.4 Hz), 5.6 (s, 2H), 4.35 (q, 2H, J=7.1 Hz), 1.35 (t, 3H, J=7.0 Hz), and 1.2 ppm (s, 9H). Elemental Analysis for C30H28F3NO4: Calculated: C, 68.82; H, 5.39; N, 2.68. Found: C, 68.84; H, 5.69; N, 2.57.

Provenance & Evidence