Potassium Phosphate, Tribasic → HCID 71272190, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	Trimethylboroxine	HCID 574072	—
Reactant	HCID 71272672	HCID 71272672	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 71272190	HCID 71272190	54.9%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 6-chloro-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (600 mg, 1.550 mmol), K3PO4 (644 mg, 3.037 mmol), PdCl2(dppf) (186 mg, 0.228 mmol), and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (290 mg, 1.52 mmol) in dioxane (2 mL) under nitrogen in a sealed vial was heated at 100° C. in a microwave oven for 18 h. The reaction mixture was quenched with EtOAc and water. The organic layer was concentrated in vacuo to afford 6-chloro-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile as white solid (230 mg, 53.9%). MS (ESI): m/z=276 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08637537B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-57cae111d5344fb79ff5a03ec679c1c0
Source note	uspto-grants-2014_01