Dichloromethane → HCID 90409158, compound

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	HCID 86299115	HCID 86299115	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Methanol	HCID 887	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 90409158	HCID 90409158	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 9-bromo-7-(3,5-dimethylisoxazol-4-yl)-4-phenyl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (9.0 mg, 0.021 mmol), phenylboronic acid (3.1 mg, 0.025 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (1:1) (0.9 mg, 0.001 mmol) and potassium carbonate (8.8 mg, 0.063 mmol) in 1,4-dioxane (0.1 mL), and water (0.07 mL) was heated at 80° C. for 3 h. The reaction mixture was diluted with MeOH and purified on by preparative LCMS using a pH 10 buffer to give the title compound. LCMS calc. for C26H22N3O3 (M+H)+: m/z=424.2. found: 424.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09227985B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-8ae31ad0b4cf4338ad351364f240e8e0
Source note	uspto-grants-2016_01