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

Participants

Role	Name	HCID	Charge
Reactant	Methyl 4-acetamido-3-iodobenzoate	HCID 15304890	—
Reactant	Benzene, 1,3-dichloro-2-ethynyl-	HCID 22271730	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-(2,6-dichloro-phenyl)-1H-indole-5-carboxylic acid methyl ester	HCID 66965953	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

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).

Provenance & Evidence

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