Ethanol → ethyl [1-benzyl-6-(3-chlorophenyl)-1H-indol-3-yl](oxo)acetate

HRID 2221231Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24](Cl)(=[O:28])[C:25](Cl)=[O:26].[CH2:30]([OH:32])[CH3:31]>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[CH:15]=2)[C:10]([C:24](=[O:28])[C:25]([O:32][CH2:30][CH3:31])=[O:26])=[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 220329421-benzyl-6-(3-chlorophenyl)-1H-indole

Product 1

HCID 22032985ethyl [1-benzyl-6-(3-chlorophenyl)-1H-indol-3-yl](oxo)acetate

Procedure

Ethyl [1-benzyl-6-(3-chlorophenyl)-1H-indol-3-yl](oxo)acetate was prepared from 1-benzyl-6-(3-chlorophenyl)-1H-indole (0.591 g, 1.86 mmol), oxalyl chloride (0.49 mL, 5.6 mmol), and ethanol (2 mL) following the procedure described in Step 3 of Example 1. Purification by flash chromatography using 5-100% ethyl acetate in hexane as an eluant yielded the title compound as a hard reddish gum (0.520 g, 67%). Mass spectrum (+ESI, [M+H]+) m/z 418; 1HNMR (500 MHz, DMSO-d6): δ 8.7 (s, 1H), 8.25 (d, 1H, J=8.2 Hz), 8.0 (s, 1H), 7.8 (s, 1H), 7.65-7.0 (m, 2H), 7.5 (t, 1H, J=7.9 Hz), 7.4 (d, 1H, J=0.92 Hz), 7.35-7.4 (m, 4H), 7.25-7.3 (m, 1H), 5.7 (s, 2H), 4.35 (q, 2H, J=7.1 Hz), and 1.35 ppm (t, 3H, J=7.2 Hz).

Workup

customPurification by flash chromatography

Sources & evidence

ORD record: ord-006d22408a7543bb9965e3e55bc98415
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368471B2

Reaction notes

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