Ethyl 4-piperidinecarboxylate → Ethyl 1-(6-chloro-4-methyl-3-pyridinyl)piperidine-4-carboxylate

HRID 528

Reaction equation

HRID 528 reaction equation
CCOC(=O)C1CCNCC1.Cc1cc(Cl)ncc1Br>CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.[Na+].[Pd]>CCOC(=O)C1CCN(c2cnc(Cl)cc2C)CC1

Participants

7

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 27344275-Bromo-2-chloro-4-methylpyridine

Product 1

HCID 82225133Ethyl 1-(6-chloro-4-methyl-3-pyridinyl)piperidine-4-carboxylateYield 0%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 4144353Palladium (II) acetateCatalystHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of diacetoxypalladium (10.87 mg, 0.05 mmol) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (45.2 mg, 0.10 mmol) dissolved in toluene (3 mL) was degassed and heated to 50°C for 30 minutes before adding ethyl piperidine-4-carboxylate (0.105 mL, 0.68 mmol), 5-bromo-2-chloro-4-methylpyridine (100 mg, 0.48 mmol) and sodium 2-methylpropan-2-olate (74.5 mg, 0.77 mmol) under nitrogen. The mixture was heated to 100°C for 2 hours. LCMS indicated little product so reaction abandoned.

Sources & evidence

ORD record
ord-e4f50ecc5cb146dc9c3dbbd5fbb158a0
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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