1,4-Dioxane → 6-(3-Methylpyridin-2-yl)-2-(4-(trifluoromethyl)phenyl)-1,2-dihydroindazol-3-one

Participants

Role	Name	HCID	Charge
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	Lithium Chloride	HCID 433294	—
Reactant	1,2-Dihydro-6-bromo-2-(4-trifluoromethylphenyl)-3H-indazol-3-one	HCID 69202774	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178479788	HCID 178479788	—
Product	6-(3-Methylpyridin-2-yl)-2-(4-(trifluoromethyl)phenyl)-1,2-dihydroindazol-3-one	HCID 11210873	54%

Reaction Steps

The product of Example 1, Step 4 (0.35 g, 1 mmol)), bis(diphenylphosphino) ferrocenyl palladium(II) dichloride 0) (40 mg), CuI (19 mg, 0.1 mmol), LiCl (126 mg, 3 mmol), 3-methyl-2-(tri-nbutylstannyl)pyridine (530 mg, 1.4 mmol) and dioxane (4 mL) were heated at 150° C. for 15 min under microwave irradiation. The resulting mixture was purified by column chromatography (silica; EtAc:hexane 1:2->EtAc) to give 0.2 g (54%) of the title compound as a colourless solid. 1H NMR (360 MHz, DMSO): 2.5 (3H, s), 7.30-7.40 (2H, m), 7.50 (1H, m), 7.78 (1H, d, J 7.7 Hz), 7.85 (1H, d, J 8.0 Hz), 7.90 (2H, d, J 8.5 Hz), 8.19 (2H, d, J 8.5 Hz), 8.53 (1H, d, J 4.6 Hz), 10.8 (1H, s).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07449585B2
Source dataset	uspto-grants-2008_11
ORD ID	ord-8d63a6f28074476e9bb2f5a93886d699
Source note	uspto-grants-2008_11