Formaldehyde → 5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Participants

Role	Name	HCID	Charge
Reactant	Formaldehyde	HCID 712	—
Reactant	Sodium triacetoxyborohydride	HCID 5049666	—
Reactant	3-(1-phenethyl-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine	HCID 90031349	—
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	—
Solvent	1,1-Dichloroethane	HCID 6365	—
Product	5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine	HCID 90031521	99%

Reaction Steps

Using similar reaction conditions as described in step-iii of example-133, 3-(1-phenethyl-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (product of step 2 of example 140) (50 mg, 0.082 mmol) was methylated using paraformaldehyde (8 mg, 0.24 mmol) and Na(OAc)3BH (35 mg, 0.164 mmol) in dichloroethane (10 mL) to afford 50 mg (99% yield) of the titled compound. MS: m/z=618.2 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-65dce79f038142e98feda3c3d38e23bd
Source note	uspto-grants-2016_05