Cesium carbonate → HCID 86699244, compound

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1-Methylpiperazine	HCID 53167	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	6-(4-Bromo-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene	HCID 86699195	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Toluene ethanol	HCID 21863594	—
Product	HCID 86699244	HCID 86699244	39%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of the corresponding 6-(4-Bromo-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.7 g, 1.5 mmol), 1-Methyl-piperazine (0.2 g, 3 mmol), Cs2CO3 (2 M, 1.5 mL), Xantphos (180 mg, 0.06 mmol) and Pd(OAc)2 (70 mg, 0.06 mmol) in toluene/ethanol (1:1, 10 mL) was heated at 100° C. for 8 hr. The solution was cooled to room temperature and extracted with ethyl acetate. The target product was purified by gravity column chromatography (50% EtOAc in hexane) to give 6-[4-(4-Methyl-piperazin-1-yl)-phenyl]-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene as brown solid in 39% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08853207B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-e17ce1f8c7004128a9f95477616e0998
Source note	uspto-grants-2014_10