Ethanol → HCID 86588617, compound

HRID 2221212Notes

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]([F:23])=[C:19]([Cl:24])[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:25](Cl)(=[O:29])[C:26](Cl)=[O:27].[CH2:31]([OH:33])[CH3:32]>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=3)=[CH:14][CH:15]=2)[C:10]([C:25](=[O:29])[C:26]([O:33][CH2:31][CH3:32])=[O:27])=[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 22032933HCID 22032933, compound

Product 1

HCID 86588617HCID 86588617, compoundYield 67%

Procedure

Ethyl [1-benzyl-5-(3-chloro-4-fluorophenyl)-1H-indol-3-yl](oxo)acetate was prepared from 1-benzyl-5-(3-chloro-4-fluorophenyl)-1H-indole (0.705 g, 2.10 mmol), oxalyl chloride (0.73 mL, 8.4 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 yellow solid (0.616 g, 67%), mp: 148-149° C. Mass spectrum (+APCI, [M+H]+) m/z 436; 1HNMR (400 MHz, DMSO-d6): δ 8.75 (s, 1H), 8.4 (d, 1H, J=2.0 Hz), 7.85 (dd, 1H, J=7.1 Hz and 2.4 Hz), 7.6-7.7 (m, 3H), 7.5 (t, 1H, J=8.9 Hz), 7.25-7.35 (m, 5H), 5.65 (s, 2H), 4.35 (q, 2H, J=7.1 Hz), and 1.35 ppm (t, 3H, J=7.1 Hz).

Workup

customPurification by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record: ord-7a0149e6dc154f39ad9e1b62b78ee925
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368471B2

Reaction notes

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