Lithium Hydroxide → tert-butyl (5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxypyridin-2-yl)carbamate

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 (5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxypyridin-2-yl)carbamate	HCID 131735680	—
Solvent	Methanol tetrahydrofuran water	HCID 21892291	—
Product	tert-butyl (5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxypyridin-2-yl)carbamate	HCID 131735681	63.9%

Reaction Steps

Using similar reaction conditions as described in step-iii of example-1, tert-butyl (5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxypyridin-2-yl)carbamate (200 mg, 0.279 mmol) was hydrolyzed by lithium hydroxide (118 mg, 2.798 mmol) in THF/methanol/water (5/5/2 ml) to yield 100 mg (63.6% yield) of the titled compound. MS: m/z=560.9 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-3b480d80b4a245259d3e3b01d0f6a2a2
Source note	uspto-grants-2016_05