Formamide → 9-bromo-N-formyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Formamide	HCID 713	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	9-Bromo-2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine	HCID 58204858	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	9-bromo-N-formyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide	HCID 58204570	46%

Reaction Conditions

Temperature	70 °C

Reaction Steps

9-bromo-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine, from Example 43, (1.0 g, 2.56 mmol), Pd(dppf)Cl2(104 mg, 0.128 mmol) and DMAP (363 mg, 2.56 mmol) were combined in a flask, and HCONH2 (30 ml) was added. The resulting mixture was stirred at 70° C. for 5 h. The reaction mixture was cooled to room temperature, diluted with EtOAc, and filtered. The solid was collected to give 9-bromo-N-formyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide (400 mg, 46%). LCMS (ESI) m/z 335.8 (M+H+)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08242104B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-05621599b5af416fa3c9eea54eb85b92
Source note	uspto-grants-2012_08