Tetrahydrofuran → 4-(2,3-Dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-quinoline

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	3-Fluoro-4-iodoquinoline	HCID 11108496	—
Reactant	1H,2H,3H-pyrrolo(3,2-c)pyridine	HCID 12490979	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Solvent	Water	HCID 962	—
Product	4-(2,3-Dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-quinoline	HCID 18440648	68.2%

Reaction Conditions

Temperature	80 °C

Reaction Steps

3-Fluoro-4-iodo-quinoline (0.2 g, 0.73 mmol) was placed in a 25 ml round bottomed flask and to it was added tetrahydrofuran (15 ml), xantphos (0.015 g, 0.02 mmol), cesium carbonate (0.476 g, 1.4 mmol), 5-azaindoline (0.087 g, 0.73 mmol). The mixture was degassed for 5 mins. Tris(dibenzylidineacetone) dipalladium(0) (0.0025 g, 0.0025 mmol) was added and the mixture was heated to 80° C. for 48 hrs. Water was and compound extracted into ethyl acetate, dried over sodium sulfate and concentrated in rotary evaporator to yield desired compound (0.132 g, 67%). MS (ES) 266.1 (M+H)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268857B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-3903226de03c44c29b8e3334f7b148a3
Source note	uspto-grants-2012_09