Ethanol → Ethyl 2-{1-benzyl-6-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl}-2-oxoacetate

HRID 2221191Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](Cl)(=[O:31])[C:28](Cl)=[O:29].[CH2:33]([OH:35])[CH3:34]>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=3)[CH:15]=2)[C:10]([C:27](=[O:31])[C:28]([O:35][CH2:33][CH3:34])=[O:29])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 702Ethanol

HCID 65578Oxalyl chloride

HCID 220329201-Benzyl-6-[4-(trifluoromethyl)phenyl]-1H-indole

Product 1

HCID 22032961Ethyl 2-{1-benzyl-6-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl}-2-oxoacetateYield 62%

Procedure

Following the procedure described in Step 3 of Example 1, ethyl 2-[1-benzyl-6-(4-trifluoromethyl)-1H-indol-3-yl]-2-oxoacetate was prepared from 1-benzyl-6-[4-(trifluoromethyl)phenyl]-1H-indole (0.392 g, 1.12 mmol), oxalyl chloride (0.11 mL, 1.2 mmol), and ethanol (1.4 mL). Purification by flash chromatography using 5-10% ethyl acetate in hexane as an eluant followed by trituration with hexane yielded the title compound as a light yellow solid (0.314 g, 62%), mp: 109-110° C. Mass spectrum (+APCI, [M+H]+) m/z 452; 1HNMR (400 MHz, DMSO-d6): δ 8.75 (s, 1H), 8.25 (d, 1H, J=8.3 Hz), 8.05 (d, 1H, J=0.98 Hz), 7.95 (d, 2H, J=8.1 Hz), 7.8 (d, 2H, J=8.3 Hz), 7.7 (dd, 1H, J=8.3 Hz and 1.5 Hz), 7.25-7.35 (m, 5H), 5.7 (s, 2H), 4.35 (q, 2H, J=7.2 Hz), and 1.35 ppm (t, 3H, J=7.1 Hz). Elemental Analysis for C26H20F3NO3.0.25 H2O: Calculated: C, 68.49; H, 4.53; N, 3.07. Found: C, 68.24; H, 4.46; N, 3.10.

Workup

customPurification by flash chromatography

Sources & evidence

ORD record: ord-486539488f6b435f80ca4eed2df4a5b1
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368471B2

Reaction notes

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