Ethanol → HCID 86588619, compound

HRID 2221228Notes

Reaction equation

HRID 2221228 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[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:28](Cl)(=[O:32])[C:29](Cl)=[O:30].[CH2:34]([OH:36])[CH3:35]>>[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:25])[F:26])=[CH:19][CH:18]=3)[CH:13]=[CH:14][CH:15]=2)[C:10]([C:28](=[O:32])[C:29]([O:36][CH2:34][CH3:35])=[O:30])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 22032970HCID 22032970, compound

Product 1

HCID 86588619HCID 86588619, compoundYield 55%

Procedure

Ethyl {1-benzyl-4-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-4-[4-(trifluoromethoxy)phenyl]-1H-indole (0.243 g, 0.661 mmol), oxalyl chloride (1.03 mL, 13.0 mmol), and ethanol (5 mL) according to the procedure described in Step 3 of Example 1. Purification was carried out by reverse phase HPLC using 22% water in acetonitrile as the mobile phase. Extraction with ethyl acetate, washing with brine, and evaporation to dryness afforded the title compound as a yellow gum (0.169 g, 55%). 1HNMR (300 MHz, DMSO-d6): δ 8.65 (s, 1H), 7.65 (d, 1H, J=7.5 Hz), 7.3-7.45 (m, 10H), 7.2 (d, 1H, J=7.5 Hz), 5.65 (s, 2H), 4.25 (q, 2H, J=7.3 Hz), and 1.35 ppm (t,3H, J=7.5 Hz).

Workup

  1. customPurification
  2. extractionExtraction with ethyl acetate
  3. washwashing with brine, and evaporation to dryness

Sources & evidence

ORD record
ord-7a45830097e5474da503fc1a253f6e93
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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