Ethanol → HCID 22032966, compound

HRID 2221222Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=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][CH:13]=[CH:14][C:15]=2[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=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 22032907HCID 22032907, compound

Product 1

HCID 22032966HCID 22032966, compoundYield 61%

Procedure

Ethyl [1-benzyl-7-(3-chloro-4-fluorophenyl)-1H-indol-3-yl](oxo)acetate was prepared from 1-benzyl-7-(3-chloro-4-fluorophenyl)-1H-indole (0.182 g, 0.542 mmol), oxalyl chloride (0.28 mL, 3.3 mmol), and ethanol (0.75 mL) following the procedure described in Step 3 of Example 1. Purification by HPLC using 20% ethyl acetate in hexane as the mobile phase yielded the title compound as a hard yellow gum (0.143 g, 61%). 1HNMR (300 MHz, DMSO-d6): δ 8.7 (s, 1H), 8.35 (d, 1H, J=7.5 Hz), 7.3-7.4 (m, 2H), 7.0-7.25 (m, 6H), 6.35 (d, 2H, J=7.5 Hz), 5.35 (d, 1H, J=15.8 Hz), 5.15 (d, 1H, J=15.8 Hz), 4.35 (q, 2H, J=7.5 Hz), and 1.35 ppm (t, 3H, J=7.5 Hz).

Workup

customPurification by HPLC

Sources & evidence

ORD record: ord-763783878c304b859cca8a937761217f
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368471B2

Reaction notes

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