Ethanol → HCID 22032954, compound

HRID 1791444Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[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:31](Cl)(=[O:35])[C:32](Cl)=[O:33].[CH2:37]([OH:39])[CH3:38]>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=[C:19]([C:27]([F:30])([F:28])[F:29])[CH:18]=3)=[CH:14][CH:15]=2)[C:10]([C:31](=[O:35])[C:32]([O:39][CH2:37][CH3:38])=[O:33])=[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 22032962HCID 22032962, compound

Product 1

HCID 22032954HCID 22032954, compoundYield 56%

Procedure

Ethyl 2-{1-benzyl-5-[3,5-bis(trifluoromethyl)phenyl]-1H-indol-3-yl}-2-oxoacetate was prepared from 1-benzyl-5-[3,5-bis(trifluoromethyl)phenyl]-1H-indole (1.07 g, 2.56 mmol), oxalyl chloride (1.3 mL, 15 mmol), and ethanol (6 mL) following the procedure described in Step 3 of Example 1. Purification by HPLC (reverse phase column) using 85% acetonitrile and 0.1% trifluoroacetic acid in water as the mobile phase yielded the title compound as a light yellow solid (0.746 g, 56%). 1HNMR (300 MHz, DMSO-d6): δ 8.8 (s, 1H), 8.5 (s, 1H), 8.3 (s, 2H), 8.1 (s, 1H), 7.75 (s, 2H), 7.25-7.4 (m, 5H), 5.65 (s, 2H), 4.35 (q, 2H, J=7.5 Hz), and 1.35 ppm (t, 3H, J=7.5 Hz).

Workup

customPurification by HPLC (reverse phase column)

Sources & evidence

ORD record: ord-174825499dbe47fc9e22acd8c0a18a7f
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074817B2

Reaction notes

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