Toluene → 2-Benzyl-6-methyl-2,3,3a,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalen-7-one

Participants

Role	Name	HCID	Charge
Reactant	Toluene	HCID 1140	—
Reactant	HCID 131729027	HCID 131729027	—
Reactant	HCID 178477796	HCID 178477796	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Benzyl-6-methyl-2,3,3a,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalen-7-one	HCID 131729028	97%

Reaction Conditions

Temperature	22 °C

Reaction Steps

A solution of the product from step e) (2.4 g, 6.89 mmol) in dioxane (34.5 ml) was treated with Pd(dppf)2Cl2 (337 mg, 0.41 mmol) and a 2M solution of dimethylzinc in toluene (6.89 ml, 13.78 mmol) at 102° C. for 1 hour. The reaction was cooled to 22° C. and carefully quenched with sat. NH4Cl (20 ml). After the effervescence subsided, the reaction was extracted with EtOAc (3×50 ml). The combined organic layers were dried (MgSO4) and passed through a plug of silica-gel using 50:50 hexanes:EtOAc to give the subtitle compound (1.9 g, 97%). MS calculated for C17H17NOS+H 284, observed 284.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07981919B2
Source dataset	uspto-grants-2011_07
ORD ID	ord-7d45e7a320324e35be752a3a51b923d5
Source note	uspto-grants-2011_07