Ethanol → HCID 86588616, compound

HRID 1791435Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH:13]=[CH:14][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](=[C:12]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=3)[CH:13]=[CH:14][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 22032904HCID 22032904, compound

Product 1

HCID 86588616HCID 86588616, compoundYield 19%

Procedure

Ethyl {1-benzyl-4-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-4-[4-(trifluoromethyl)phenyl]-1H-indole (0.257 g, 0.731 mmol), oxalyl chloride (2.2 mL, 26 mmol), and ethanol (6 mL) according to the procedure described in Step 3 of Example 1. Purification by HPLC using 3% ethanol in hexane as the mobile phase afforded the title compound as a hard yellow gum (0.064 g, 19%). 1HNMR (200 MHz, DMSO-d6): δ 8.7 (s, 1H), 7.7 (d, 3H, J=7.7 Hz), 7.15-7.5 (m, 9H), 5.65 (s, 2H), 4.25 (q, 2H, J=7.0 Hz), and 1.35 ppm (t, 3H, J=7.1 Hz).

Workup

customPurification by HPLC

Sources & evidence

ORD record: ord-7c980a79f7864a7aba53e17c86104c1e
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074817B2

Reaction notes

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