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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 531763Generated: October 26, 2026

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

https://huagongshe.com/reaction/531763

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormaldehydeHCID 712—
ReactantSodium triacetoxyborohydrideHCID 5049666—
Reactant3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 90030300—
Reactant3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochlorideHCID 118524085—
Solvent1,1-DichloroethaneHCID 6365—
Product3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 9003363488.2%

Reaction Steps

Using similar reaction conditions as described in step-iii of example-133, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.164 mmol) was methylated using paraformaldehyde (15 mg, 0.494 mmol) and Na(OAc)3BH (105 mg, 0.494 mmol) in dichloroethane (5 mL) to afford 90 mg (88.2% yield) of the titled compound after purification by column (Silica gel 60/120) using 5% methanol in dichloromethane as eluent. MS: m/z=622.1 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09353107B2
Source datasetuspto-grants-2016_05
ORD IDord-3243d6c096d94ecd9097e504acf03e61
Source noteuspto-grants-2016_05