Cesium carbonate → Tert-butyl 4-(5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	tert-Butyl piperazine-1-carboxylate	HCID 143452	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	1H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(3-methoxyphenyl)-1-(phenylsulfonyl)-	HCID 68760387	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Toluene	HCID 1140	—
Product	Tert-butyl 4-(5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate	HCID 68761257	29.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

4-Chloro-5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyri dine (0.400 g, 1.00 mmol), tert-butyl piperazine-1-carboxylate (0.280 g, 1.50 mmol), Pd(OAc)2 (0.0225 g, 0.100 mmol), Xantphos (0.0870 g, 0.150 mmol), and Cs2CO3 (0.490 g, 1.50 mmol) were placed in degassed toluene (4 mL). The mixture was heated to 100° C. for 24 hours. The reaction was cooled to room temperature, filtered through celite, and concentrated. The product was purified (500:5 to 500:7 DCM:MeOH) to yield tert-butyl 4-(5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazine-1-carboxylate (0.160 g, 29.0% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08841304B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-9485091727a042dd83558ff672d029d0
Source note	uspto-grants-2014_09