Cesium carbonate → 4-(Cyclopent-1-en-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	2-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 15486611	—
Reactant	4-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole	HCID 16216709	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Product	4-(Cyclopent-1-en-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole	HCID 89963017	85%

Reaction Steps

The reaction and aftertreatment were conducted in the same manner as in Example 39a by using 4-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (J. Org. Chem., 2007, 72 (9), 3589-3591; 1.51 g, 5.42 mmol), 2-cyclopent-1-en-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.37 g, 7.05 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (317 mg, 0.434 mmol), cesium carbonate (6.01 g, 18.4 mmol), dioxane (27 mL) and water (5.0 mL), to yield the title compound (1.00 g, 85%) as a colorless oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08889741B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-24bbe138a72d48e2a17ed9be1255ef5f
Source note	uspto-grants-2014_11