Cesium carbonate → 4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-1-[2-(methylsulfonyl)quinolin-6-yl]piperazin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	6-Bromo-2-(methylsulfonyl)quinoline	HCID 12378934	—
Reactant	4-[(2R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-2-one	HCID 117612700	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-1-[2-(methylsulfonyl)quinolin-6-yl]piperazin-2-one	HCID 89535509	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-2-one (66 mg, 0.23 mmol), 6-Bromo-2-(methylsulfonyl)quinoline [I-14] (65 mg, 0.23 mmol), Pd2(dba)3 (42 mg, 0.045 mmol), Xantphos (53 mg, 0.091 mmol), and Cs2CO3 (110 mg, 0.34 mmol) in DMF (5 mL) was sealed in a microwave tube and purged three times with nitrogen. It was heated to 120° C. for 10 minutes in a microwave reactor. LC showed formation of the product. The material was purified by silica gel flash chromatography, followed by crystallization to give the title product. LC-MS (IE, m/z): 496 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08999991B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-9cf66603d17145a1b31620f6a6d7c3ff
Source note	uspto-grants-2015_04