Tetrahydrofuran → N-((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)oxazole-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 11587208	—
Reactant	(S)-2-bromo-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)oxazole-4-carboxamide	HCID 70656701	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)oxazole-4-carboxamide	HCID 70656357	31.4%

Reaction Conditions

Temperature	100 °C

Reaction Steps

(S)-2-bromo-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)oxazole-4-carboxamide (153 mg, 0.352 mmol), 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-5-boronic acid pinacol ester (490 mg, 1.760 mmol), tetrakis(triphenylphosphine)palladium (4.07 mg, 3.52 umol), THF and 2 M Na2CO3 solution were added in a microwave flask and heated at 100° C. for 1 h. The reaction mixture was diluted with DCM and washed twice with NaHCO3 solution. Organic phase was dried and evaporated to dryness. The product was purified twice by Flash-chromatography. Yield 31.4%. m/z [506.0+1].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08975254B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-b51f0700655044e4b858545deff9fd57
Source note	uspto-grants-2015_03