Cesium carbonate → Tert-butyl 4-(7-cyanoisoquinolin-3-yl)-3-oxopiperazine-1-carboxylate

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	Tert-butyl 3-oxopiperazine-1-carboxylate	HCID 3157178	—
Reactant	3-Chloroisoquinoline-7-carbonitrile	HCID 84819605	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Tert-butyl 4-(7-cyanoisoquinolin-3-yl)-3-oxopiperazine-1-carboxylate	HCID 89525285	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a flask charged with 3-chloroisoquinoline-7-carbonitrile (250 mg, 1.3 mmol) and a stir bar was added tert-butyl 3-oxopiperazine-1-carboxylate (400 mg, 2.0 mmol), Pd2(dba)3 (120 mg, 0.13 mmol), Xantphos (150 mg, 0.26 mmol), cesium carbonate (650 mg, 2.0 mmol), and dioxane (20 mL). The mixture was purged three times with nitrogen, and heated to 100° C. for 16 hours. The mixture was diluted with EtOAc, washed with brine, dried over sodium sulfate, adsorbed onto silica gel, and purified by silica gel chromatography (Hexanes:EtOAc) to provide tert-butyl 4-(7-cyanoisoquinolin-3-yl)-3-oxopiperazine-1-carboxylate. LC-MS (IE, m/z): 353 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08999991B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-e99bc2b2a71e4dcbaee2175cbb7c4458
Source note	uspto-grants-2015_04