Ethanol → HCID 69492773, compound

HRID 2221209Notes

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]([CH3:26])([CH3:25])[CH3:24])=[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:18]=[CH:19][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:21][CH:22]=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

Reactant 3

HCID 702Ethanol

HCID 65578Oxalyl chloride

HCID 22032917HCID 22032917, compound

Product 1

HCID 69492773HCID 69492773, compoundYield 71%

Procedure

Ethyl {1-benzyl-5-[4-(tert-butyl)phenyl]-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-5-[4-(tert-butyl)phenyl]-1H-indole (0.732 g, 2.16 mmol), oxalyl chloride (0.75 mL, 8.6 mmol), and ethanol (6 mL) according to the procedure described in Step 3 of Example 1. Purification by flash chromatography (Biotage apparatus) using 5-10% ethyl acetate in hexane as an eluant afforded the title compound as a light yellow solid (0.671 g, 71%). 1HNMR (200 MHz, DMSO-d6): δ 8.7 (s, 1H), 8.4 (s, 1H), 7.45-7.7 (m, 6H), 7.35 (s, 5H), 5.65 (s, 2H), 4.35 (q, 2H, J=6.7 Hz), and 1.3-1.45 ppm (m, 12H).

Workup

customPurification by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record: ord-94a145ab5bfd4f808bffe50662b7160d
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368471B2

Reaction notes

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