Lithium Hydroxide → tert-butyl 4-((4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)amino)piperidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Lithium Hydroxide	HCID 3939	—
Reactant	3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride	HCID 118524085	—
Reactant	tert-butyl 4-((4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)amino)piperidine-1-carboxylate	HCID 118524105	—
Solvent	Methanol tetrahydrofuran water	HCID 21892291	—
Product	tert-butyl 4-((4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)amino)piperidine-1-carboxylate	HCID 118523931	58.8%

Reaction Steps

Using similar reaction conditions as described in step-iii of example-1, tert-butyl 4-((4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)amino)piperidine-1-carboxylate (130 mg, 0.18 mmol) was hydrolyzed with lithium hydroxide (37 mg, 0.9 mmol) in THF/methanol/water (2/2/1 mL) to yield 60 mg (58.8% yield) after purification by preparative TLC (Silicagel-1000 micron) using 3% methanol in chloroform as eluent. MS: m/z=566.8 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-bc6828a3ea594027a81d6d9a1c4297ca
Source note	uspto-grants-2016_05