Potassium Carbonate → 4-(Cyclopent-1-en-1-yl)-3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 15486611	—
Reactant	4-bromo-3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole	HCID 66652794	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-(Cyclopent-1-en-1-yl)-3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole	HCID 89962894	89.1%

Reaction Steps

The reaction and aftertreatment were conducted in the same manner as in Example 33a by using 4-bromo-3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (WO 2010/079443; 1.20 g, 4.35 mmol), 2-cyclopent-1-en-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.20 g, 6.18 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (250 mg, 0.342 mmol), potassium carbonate (2.00 g, 14.5 mmol) and DMF (13 mL), to yield the title compound (1.02 g, 89%) as a yellow oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08889741B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-df20e8a59876438a99a5a62b0711ac4e
Source note	uspto-grants-2014_11