Potassium Carbonate → 5-Methoxy-1-phenyl-1H-indole

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Iodobenzene	HCID 11575	—
Reactant	5-Methoxyindole	HCID 13872	—
Reactant	L-Proline	HCID 145742	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	5-Methoxy-1-phenyl-1H-indole	HCID 13603429	62.7%

Reaction Conditions

Temperature	125 °C

Reaction Steps

To a mixture of 5-methoxyindole (1.00 g, 6.79 mmol), copper(I) iodide (129 mg, 0.68 mmol), L-proline (156 mg, 1.36 mmol) and potassium carbonate (1.88 g, 13.6 mmol) in DMSO (7.5 ml) was added iodobenzene (0.76 ml, 6.79 mmol). The reaction mixture was stirred for 10 h at 125° C. in a microwave reactor. The mixture was then quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (EA/HEP 1:15). 951 mg of the title compound were obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08211885B2
Source dataset	uspto-grants-2012_07
ORD ID	ord-bbe2d10967f7493cae6f06ed057b4501
Source note	uspto-grants-2012_07