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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2203757Generated: October 30, 2026

(3R)-3-Aminopiperidine, 3-BOC protected → (R)-tert-butyl 1-(5-bromo-3-isobutyramido-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate

https://huagongshe.com/reaction/2203757

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(3R)-3-Aminopiperidine, 3-BOC protectedHCID 1514172—
ReactantN-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)isobutyramideHCID 60205321—
Solvent1-ButanolHCID 263—
Product(R)-tert-butyl 1-(5-bromo-3-isobutyramido-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamateHCID 6704508747%

Reaction Conditions

Temperature160 °C

Reaction Steps

(R)-tert-Butyl piperidin-3-ylcarbamate (327 mg, 1.63 mmol) was added to N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)isobutyramide (140 mg) in n-BuOH (3 mL), and the reaction was stirred at 160° C. for 24 hours in a sealed tube. The reaction was concentrated to dryness. Then the residue was purified by C-18 reverse phase flash chromatography (Biotage SP4 unit, C-18 25M column, 10-90% gradient CH3CN/water gradient; CV) to yield (R)-tert-butyl 1-(5-bromo-3-isobutyramido-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3ylcarbamate (105 mg, 47% yield) as a solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365568B2
Source datasetuspto-grants-2016_06
ORD IDord-abf01b1dd98f4dbc94411a8878cb2eec
Source noteuspto-grants-2016_06