Water → 1-(4-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)-1H-imidazol-1-yl)-2-methylpropan-2-ol

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	1,2-Dimethoxyethane	HCID 8071	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1-(4-bromo-1H-imidazol-1-yl)-2-methylpropan-2-ol	HCID 58204340	—
Reactant	2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine	HCID 58204713	—
Reactant	1-(5-bromo-1H-imidazol-1-yl)-2-methylpropan-2-ol	HCID 58204721	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	1-(4-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)-1H-imidazol-1-yl)-2-methylpropan-2-ol	HCID 58205023	12%

Reaction Steps

2-(1-Isopropyl-1H-1,2,4-triazol-5-yl)-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (113 mg, 0.268 mmol), 1-(4-bromo-1H-imidazol-1-yl)-2-methylpropan-2-ol and 1-(5-bromo-1H-imidazol-1-yl)-2-methylpropan-2-ol (88.14 mg, 0.40 mmol), 1,1′-Bis(diphenylphosphino)ferrocenepalladium(II)chloride (21.90 mg, 0.027 mmol), 1,2-dimethoxyethane (3.0 mL, 29 mmol), and 1 M Cesium carbonate in water (0.54 mL, 0.5 mmol) were mixed in a microwave vial and microwaved at 140° C. for 15 minutes. Complete reaction by LCMS. Filtered through a paper filter followed by a silica plug. Concentrated in vacuo and purified by HPLC to give 202 (13.7 mg, 12% yield)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08343955B2
Source dataset	uspto-grants-2013_01
ORD ID	ord-073c7a24f0ef4efba469b1f88c244219
Source note	uspto-grants-2013_01