4-Fluoroiodobenzene → Methyl 3-fluoro-1-(4-fluorophenyl)-1H-indole-6-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	4-Fluoroiodobenzene	HCID 9605	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	1-N,2-N-dimethylcyclohexane-1,2-diamine	HCID 551074	—
Reactant	methyl 3-fluoro-1H-indole-6-carboxylate	HCID 59625843	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Methyl 3-fluoro-1-(4-fluorophenyl)-1H-indole-6-carboxylate	HCID 59625701	—

Reaction Conditions

Temperature	95 °C

Reaction Steps

Compound 69a (0.264 mmol, 51 mg), CuI (0.0264 mmol, 5 mg) and K3PO4 (0.66 mmol, 40 mg) were combined in a sealed reaction tube and the vial was back-flushed with N2. 4-fluoro-iodobenzene 69b (0.264 mmol, 0.0394 mL) and N,N′-dimethylcyclohexane-1,2-diamine (0.0792 mmol, 0.0125 mL) were added via sringe, followed by toluene. The reaction mixture was heated at 95° C. for 6 h. The reaction was diluted with EtOAc and water. The reaction mixture was concentrated and purified by flash column chromatography (silica gel, 20% EtOAc/hexanes) to give compound 69c.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08623858B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-ebde23f4776249a38692f6bae74e5912
Source note	uspto-grants-2014_01