Dichloromethane → 5-{5-[(4-benzyl-4-hydroxypiperidin-1-yl)methyl]2-thienyl}2-tertbutylisothiazol-3(2H)-one 1,1-dioxide trifluoroacetate

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Tert-butyl-5-chloro-2,3-dihydro-1lambda6,2-thiazole-1,1,3-trione	HCID 21878638	—
Reactant	{5-[(4-Benzyl-4-hydroxypiperidin-1-yl)methyl]-2-thienyl}boronic acid trifluoroacetate	HCID 69597789	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-{5-[(4-benzyl-4-hydroxypiperidin-1-yl)methyl]2-thienyl}2-tertbutylisothiazol-3(2H)-one 1,1-dioxide trifluoroacetate	HCID 69597881	17%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A solution of 4.12-A (100 mg, 0.2 mmol), 9-A (55 mg, 0.25 mmol), potassium carbonate (190 mg, 1.3 mmol) in 1,4-dioxane (1.5 mL) was added to a vial and degassed with nitrogen. Then [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (28 mg, 0.034 mmol) was added, degassed with nitrogen and the vial capped and heated at 80° C. overnight. The reaction mixture was filtered through silica gel and eluted with copious amounts of EtOAc. The solvent was concentrated and crude sample purified by reverse phase HPLC to afford 20 mg (15%) of 4.12-B. LCMS found for C24H30N2O4S2 (M+H)+: m/z=475.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07141596B2
Source dataset	uspto-grants-2006_11
ORD ID	ord-5da0916eddb9466d8523fdbf9746e7dc
Source note	uspto-grants-2006_11