1-Bromo-3-chlorobenzene → HCID 59264586, compound

Participants

Role	Name	HCID	Charge
Reactant	1-Bromo-3-chlorobenzene	HCID 7928	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Isobutyl piperazine-1-carboxylate	HCID 11788701	—
Reactant	sodium 2-methylpropan-2-olate	HCID 178418730	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 59264586	HCID 59264586	—

Reaction Conditions

Temperature	140 °C

Reaction Steps

3-bromo chlorobenzene (434 mg, 2.3 mmol), isobutyl piperazine-1-carboxylate 6 (324 mg, 1.7 mmol), Pd2(dba)3 (32 mg, 0.035 mmol), t-BuONa (251 mg, 2.6 mmol), and Xantphos (60 mg, 0.11 mmol) in dry toluene (5 mL) were sealed in a microwave vessel and heated by microwave irradiation at 140° C. for 40 seconds. The reaction mixture was cooled and diluted with 10 mL of CH2Cl2, washed with water (5 mL), dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)); LC/MS: m/z 297.4 (M+H)+, r.t: 3.84 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), to give 13.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07705002B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-e13ba9e2ad1b4c169acd15298a539a5e
Source note	uspto-grants-2010_04