Diethyl Ether → 1-ethyl-2-(3-hydroxy-phenyl)-6-methoxy-1H-indole-3-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Diethyl Ether	HCID 3283	—
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	3-Iodophenol	HCID 12272	—
Reactant	1-ethyl-6-methoxy-2-tributylstannanyl-1H-indole-3-carbonitrile	HCID 59424949	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	1-ethyl-2-(3-hydroxy-phenyl)-6-methoxy-1H-indole-3-carbonitrile	HCID 59426406	72%

Reaction Conditions

Temperature	65 °C

Reaction Steps

1-Ethyl-6-methoxy-2-tributylstannanyl-1H-indole-3-carbonitrile (1.0 g, 2.05 mmol), prepared in step A, was combined with 3-iodophenol (474 mg, 2.15 mmol), Pd(PPh3)2Cl2 (67 mg, 0.102 mmol), CuI (75 mg, 0.39 mmol) and THF (4.0 mL). This mixture was heated at 65° C. overnight. The reaction mixture was diluted in EtOAc, and was filtered through celite. The filtrate was concentrated and the residue was purified by silica gel chromatography (4:1, CH2Cl2/EtOAc) to yield crude product. Ether trituration yielded 1-ethyl-2-(3-hydroxy-phenyl)-6-methoxy-1H-indole-3-carbonitrile (430 mg, 72%) as a yellow-white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08013006B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-2b219baaae434ae884a40e852b6d753f
Source note	uspto-grants-2011_09