Potassium Phosphate, Tribasic → 3-(3,6-Dihydro-2H-pyran-4-yl)-5-nitro-1-trityl-1H-indazole

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester	HCID 11218053	—
Reactant	3-bromo-5-nitro-1-trityl-1H-indazole	HCID 58946443	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	3-(3,6-Dihydro-2H-pyran-4-yl)-5-nitro-1-trityl-1H-indazole	HCID 67419494	64.8%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture containing 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (0.8 g, 3.8 mmol), 3-Bromo-5-nitro-1-trityl-1H-indazole (2 g, 4.0 mmol), PdCl2(dppf) (150 mg, 0.2 mmol) and potassium phosphate (2.6 g, 12 mmol) in dioxane (10 mL) was flushed with Ar and was heated at 80° C. for overnight under Ar. LC-MS indicated the completion of reaction and the mixture was filter through celite. The filtrate was concentrated and was purified on a column (10 hexane in dichloromethane) to give 1.2 g of product (64% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546404B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-62fe18cefa354e28922bd7eac6e91492
Source note	uspto-grants-2013_10