Ethanol → HCID 69248326, compound
Reaction equation
[C:1]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=4)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:32](Cl)(=[O:36])[C:33](Cl)=[O:34].[CH2:38]([OH:40])[CH3:39]>>[CH2:38]([O:40][C:32](=[O:36])[C:33]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:28])([F:29])[F:27])=[CH:21][CH:20]=3)[CH:14]=2)[N:10]([CH2:9][C:8]2[CH:30]=[CH:31][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=2)[CH:11]=1)=[O:34])[CH3:39]Participants
Procedure
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.
Workup
- customPurification by reverse phase
- customby drying for 12 hours at 82° C.
Sources & evidence
- ORD record
- ord-f08193a8e3254b4b9b2f7096a96833d2
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368471B2
Reaction notes
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