Methyl 4-acetamido-3-iodobenzoate → 2-(2,6-dichloro-phenyl)-1H-indole-5-carboxylic acid methyl ester

HRID 1514925Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=O)[CH3:12])=[C:6](I)[CH:5]=1.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1C#C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.O1CCOCC1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][CH:5]=1)[NH:10][C:11]([C:18]1[C:17]([Cl:16])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:23])=[CH:12]2)=[O:15]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-acetylamino-3-iodo-benzoic acid methyl ester (0.17 g) in TMG (1.5 mL) and dioxane (1.5 mL) were added 1,3-dichloro-2-ethynyl-benzene (0.1 g), 10 mol % of Pd(PPh3)2Cl2, and 10 mol % of CuI. The reaction mixture was heated to 100° C. overnight. The solvent were evaporated and the resulting mixture was purified by column chromatography (SiO2, 2:3, EtOAc/Hexane) to give 2-(2,6-dichloro-phenyl)-1H-indole-5-carboxylic acid methyl ester: MS (m/z) 320.0 (M+1).

Workup

customThe solvent were evaporated
customthe resulting mixture was purified by column chromatography (SiO2, 2:3, EtOAc/Hexane)

Sources & evidence

ORD record: ord-20d199b16bd44066b1d6540add1ca3a6
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222248B2

Reaction notes

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