Cesium carbonate → 1-Methyl-N-[2-methyl-4-(trifluoromethyl)phenyl]-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-amine

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	4-Amino-3-methylbenzotrifluoride	HCID 13750437	—
Reactant	4-Chloro-1-methyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridine	HCID 57841040	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1-Methyl-N-[2-methyl-4-(trifluoromethyl)phenyl]-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-amine	HCID 57840921	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 4-chloro-1-methyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridine (100 mg), 2-methyl-4-trifluoromethylaniline (60 μl), cesium carbonate (163 mg), tris(dibenzylideneacetone)dipalladium (0) (7 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (5 mg) in 1,4-dioxan (2 ml) was heated to 100° C. under argon overnight. The reaction mixture was diluted with dichloromethane and washed with water followed by saturated sodium chloride solution, then dried (MgSO4), filtered and evaporated. Purification and salt formation was as described in Example 101 to afford the title compound as a white solid (52 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07589206B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-1d84c94010124a2e823a584a3d911e90
Source note	uspto-grants-2009_09