Ethanol → Ethyl 2-{1-benzyl-5-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl}-2-oxoacetate

HRID 2221195Notes

Reaction equation

HRID 2221195 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[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](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=3)=[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

4

Reactant 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 220329501-Benzyl-5-[4-(trifluoromethyl)phenyl]-1H-indole

Product 1

HCID 22032926Ethyl 2-{1-benzyl-5-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl}-2-oxoacetate

Procedure

Ethyl 2-{1-benzyl-5-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl}-2-oxoacetate was prepared from 1-Benzyl-5-[4-(trifluoromethyl)phenyl]-1H-indole (0.307 g, 0.874 mmol), oxalyl chloride (0.29 mL, 3.3 mmol), and ethanol (3 mL) following the procedure described in Step 3 of Example 1. The compound was purified by flash chromatography using 10-20% ethyl acetate in hexane as an eluant and dried for 20 minutes at 60° C. to give a light yellow solid (0.249 g, 63%), mp: 99-100° C. 1HNMR (200 MHz, DMSO-d6): δ 8.8 (s, 1H), 8.5 (s, 1H), 7.6-7.95 (m, 6H), 7.25-7.4 (m, 5H), 5.65 (s, 2H), 4.35 (q, 2H, J=7.7 Hz), and 1.35 ppm (t, 3H, J=7.7 Hz).

Workup

  1. customThe compound was purified by flash chromatography
  2. customdried for 20 minutes at 60° C.

Sources & evidence

ORD record
ord-7b0460fc54484147a9b376ff550e0a1e
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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