Methanol → tert-Butyl 4-(5-(3-fluorophenyl)-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Lithium Hydroxide	HCID 3939	—
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	1-Piperazinecarboxylic acid, 4-[5-(3-fluorophenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-, 1,1-dimethylethyl ester	HCID 68762198	—
Solvent	Water	HCID 962	—
Product	tert-Butyl 4-(5-(3-fluorophenyl)-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazine-1-carboxylate	HCID 68762149	92.3%

Reaction Conditions

Temperature	50 °C

Reaction Steps

tert-Butyl 4-(5-(3-fluorophenyl)-1-(phenyl sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.220 g, 0.410 mmol) was placed in 1:1 THF:MeOH (6 mL). 3M LiOH (0.683 mL, 2.05 mmol) was then added, and the reaction was stirred at 50° C. for 1 hour. The reaction was then cooled, added to water and extracted with DCM. The organic fractions were dried, filtered and concentrated to give the crude product tert-butyl 4-(5-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.150 g, 92.29% yield), which was used without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08841304B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-c2ad9115341940e8a9d885fe09601dba
Source note	uspto-grants-2014_09