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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 159Generated: October 23, 2026

Methyl 3-bromobenzoate → Methyl 3-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}benzoate

https://huagongshe.com/en/reaction/159

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl 3-bromobenzoateHCID 12070—
Reactant4-(N-Boc-amino)piperidineHCID 723833—
ReagentCesium carbonateHCID 10796—
CatalystBinap, (A+-)-HCID 634876—
CatalystPalladium (II) acetateHCID 4144353—
SolventTolueneHCID 1140—
ProductMethyl 3-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}benzoateHCID 6858003613.76%

Reaction Conditions

Temperature100 °C

Reaction Steps

All chemicals were mixed in a 50 mL round bottom flask. The solids were degassed and placed under nitrogen. Toluene was added and the mixture was stirred at 100°C for 24 h. Cooled and filtered. The filtrate was concentrated under vacuum. Crude product was mainly starting material but some product had been formed. The product was purified by silica gel chromatography using 1-4% methanol/DCM. Product was slightly more polar than starting material bromide. There was obtained 230 mg of the desired product as a solid. HNMR and LC MS ok.

Provenance & Evidence

Source dataset750 AstraZeneca ELN dataset
ORD IDord-2de77de369ef42f8b910f9e83130f454
Source note750 AstraZeneca ELN dataset