Dichloromethane → 3-(4-Fluorophenyl)-5-nitro-1H-indazole

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Fluorophenylboronic acid	HCID 285645	—
Reactant	1-Boc-3-bromo-5-nitro-1H-indazole	HCID 22260836	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	3-(4-Fluorophenyl)-5-nitro-1H-indazole	HCID 53439742	100%

Reaction Conditions

Temperature	95 °C

Reaction Steps

The product from Step (b) (0.5 g, 1.5 mmol), 4-fluoro phenylboronic acid (0.31 g, 2.2 mmol) and Pd(dppf)2Cl2.CH2Cl2 (0.12 g, 0.15 mmol) were combined in 9 ml of 2:1 Dioxane/2 M K2CO3 The reaction mixture was sealed and heated to 95° C. for 18 h. The resulting biphasic mixture was cooled to room temperature. The phases were separated and the organic phase (top) was filtered. The aqueous layer was extracted once with EtOAc. The combined organic phases were washed with sat'd NaHCO3, water, brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (5% MeOH/CH2Cl2) to afford 0.37 g of the title compound, (100%); MS (ES+) m/e 259 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07560467B2
Source dataset	uspto-grants-2009_07
ORD ID	ord-26ae3449e1e54625a1aa31e2d7e2bb03
Source note	uspto-grants-2009_07