Triethyl phosphite → methyl 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylate

HRID 1514942Notes

Reaction equation

HRID 1514942 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[C:6]([N+:20]([O-])=O)[CH:5]=1.C(OP(OCC)OCC)C>>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[C:11]1[NH:20][C:6]2[C:7]([CH:10]=1)=[CH:8][CH:9]=[C:4]([C:3]([O:2][CH3:1])=[O:23])[CH:5]=2

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 669657434-[(E)-2-(2,6-dichlorophenyl)-vinyl]-3-nitrobenzoic acid methyl ester

Product 1

HCID 66965661methyl 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylate

Conditions

Temperature
162 °C

Procedure

A mixture of 4-[(E)-2-(2,6-dichlorophenyl)-vinyl]-3-nitrobenzoic acid methyl ester (1.6 g, 4.5 mmol) and triethylphosphite (7.7 g, 6 equiv.) was heated at 162° C. for 3 h. Excess triethylphosphite was removed under reduced pressure and the redidual oil was purified by chromatography using methylene chloride as eluent to give methyl 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylate as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 11.88 (s, 1H), 8.05 (s, 1H), 7.71-7.65 (m, 4H), 7.65-7.53 (m, 1H), 6.63 (s, 1H), 3.87 (s, 3H). MS (m/z) 320.07 (M+1).

Workup

  1. customExcess triethylphosphite was removed under reduced pressure
  2. customthe redidual oil was purified by chromatography

Sources & evidence

ORD record
ord-40ea9a796ce34d6aa6320fc81fac94d3
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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