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

HRID 159
Notes
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Reaction equation

HRID 159 reaction equation
CC(C)(C)OC(=O)NC1CCNCC1.COC(=O)c1cccc(Br)c1>CC(=O)O.CC(=O)O.Cc1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>COC(=O)c1cccc(N2CCC(NC(=O)OC(C)(C)C)CC2)c1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 12070Methyl 3-bromobenzoateHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 68580036Methyl 3-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}benzoateYield 13.76%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 634876Binap, (A+-)-Catalyst
On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
HCID 4144353
Palladium (II) acetate
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Sources & evidence

ORD record
ord-2de77de369ef42f8b910f9e83130f454
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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