Dichloromethane → 5-(6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)-1-methyl 1H-pyrazole-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	1,8-Diazabicyclo(5.4.0)undec-7-ene	HCID 81184	—
Reactant	(Methanesulfinyl)methane--water (1/1)	HCID 23503278	—
Reactant	5-Bromo-1-methyl-1H-pyrazole-4-carbonitrile	HCID 53429274	—
Reactant	6-(3,5-Dimethylisoxazol-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one	HCID 123296709	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	5-(6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)-1-methyl 1H-pyrazole-4-carboxamide	HCID 117601072	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a microwave vial containing 6-(3,5-dimethylisoxazol-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (100 mg, 0.28 mmol, 1 equiv.) was added 5-bromo-1-methyl-1H-pyrazole-4-carbonitrile (130 mg, 0.30 mmol, 2.5 equiv.), Pd(dppf)Cl2.CH2Cl2 (23 mg, 0.03 mmol, 0.1 equiv.) and DBU (253 μL, 1.69 mmol, 6 equiv.) and dissolved in DMSO-H2O (4 mL, 0.2 M, 2/1, v/v). The mixture was heated to 120° C. for 30 min in microwave. The reaction was concentrated in vacuo and purification was then carried out by reverse phase HPLC.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09255089B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-3060c97c352f4e109e4f5dfcb7340b10
Source note	uspto-grants-2016_02