1,2-Diaminocyclohexane → [1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	1,2-Diaminocyclohexane	HCID 4610	—
Reactant	1-Chloro-4-iodobenzene	HCID 12510	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	methyl 2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate	HCID 67218699	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	[1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester	HCID 67220030	—

Reaction Conditions

Temperature	160 °C

Reaction Steps

A mixture of (2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester (100 mg, 0.49 mmol), 1-chloro-4-iodo-benzene (117 mg, 0.49 mmol), CuI (5 mg, 0.03 mmol), cyclohexane-1,2-diamine (6 μL, 0.05 mmol), potassium phosphate (218 mg, 1.0 mmol) and 1,4-dioxane (0.5 mL) is heated at 160° C. for 140 minutes. The reaction is cooled, diluted with EtOAc, filtered through silica and evaporated to dryness. The residue is purified by flash column chromatography (5:1 iso-hexane/EtOAc elution) to furnish [1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester; MH+=315.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08455645B2
Source dataset	uspto-grants-2013_06
ORD ID	ord-28004e39bb964b3a86b28926882689f9
Source note	uspto-grants-2013_06