Morpholine → 5-(4-Methoxy-benzyl)-7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione

Participants

Role	Name	HCID	Charge
Reactant	Morpholine	HCID 8083	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	7-Chloro-5-(4-methoxy-benzyl)-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione	HCID 90421837	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-(4-Methoxy-benzyl)-7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione	HCID 86295847	39.7%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 7-chloro-5-(4-methoxy-benzyl)-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione (65 mg, 0.141 mmol, see Example c7)), morpholine (12.31 mg, 0.141 mmol), Xantphos (82 mg, 0.141 mmol), palladium diacetate (31.7 mg, 0.141 mmol) and Cs2CO3 (138 mg, 0.424 mmol) in dioxane (5 ml) was heated in a CEM microwave at about 120° C. for about 30 min. The solvent was removed and the crude material was purified via preparative thin-layer chromatography (MeOH/DCM=5:95) to give the title compound (30 mg, 0.056 mmol, 39.5% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09163019B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-afff9f16ec1941a6acae0c6be6d4f8aa
Source note	uspto-grants-2015_10