Ethyl Acetate → HCID 66820277, compound

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline	HCID 16217914	—
Reactant	4-[6,7-Bis(methyloxy)quinolin-4-yl]-7-bromo-2,3,4,5-tetrahydro-1,4-benzoxazepine	HCID 66819980	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	HCID 66820277	HCID 66820277	63%

Reaction Steps

A mixture 4-[6,7-bis(methyloxy)quinolin-4-yl]-7-bromo-2,3,4,5-tetrahydro-1,4-benzoxazepine (78 mg, 0.19 mmol), 4-amino-3-nitrophenylboronic acid pinacol ester (59 mg, 0.23 mmol), potassium carbonate (105 mg, 0.76 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (20 mg, 0.02 mmol) in dimethoxyethane (3 mL) was stirred at 80° C. for 3 h. Ethyl acetate (50 mL) was added and the mixture was washed with water (20 mL), and brine (20 mL), dried over sodium sulfate, and concentrated. Column chromatography on silica (dichloromethane:methanol 95:5) gave 4-{4-[6,7-bis(methyloxy)quinolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}-2-nitroaniline (56 mg, 63% yield). MS (EI) for C26H24N4O5: 473 (MH+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08648066B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-2878c72d97e0445896b4cf842ea621cf
Source note	uspto-grants-2014_02