tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)-5,6-di hydropyridine-1(2H)-carboxylate → tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)piperidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)-5,6-di hydropyridine-1(2H)-carboxylate	HCID 118523940	—
Catalyst	Palladium hydroxide	HCID 9942167	—
Solvent	1-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 53440213	—
Product	tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)piperidine-1-carboxylate	HCID 118524078	99%

Reaction Steps

Using similar reaction conditions as described in step-ii of example-82, tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)-5,6-di hydropyridine-1(2H)-carboxylate (103 mg, 0.139 mmol) was reduced with palladium hydroxide (50 mg) in ethyl acetate/ethanol 5/15 mL to afford 102 mg (99% yield) of the titled compound. MS: m/z=742.6 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-e097b24aedb84f2088cee842af6b7da0
Source note	uspto-grants-2016_05