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

HRID 527

Reaction equation

HRID 527 reaction equation
CCOC(=O)C1CCNCC1.Cc1cc(Cl)ncc1Br>CC(C)(C)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[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 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.18 mg, 0.02 mmol) was added to a degassed mixture of ethyl piperidine-4-carboxylate (0.105 mL, 0.68 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)(xantphos) (28.0 mg, 0.05 mmol) and ethyl 1-(6-chloro-4-methylpyridin-3-yl)piperidine-4-carboxylate and sodium 2-methylpropan-2-olate (65.2 mg, 0.68 mmol) in toluene (3 mL). The resulting suspension was stirred at 100 °C for 20 hours under nitrogen. LCMS indicated little reaction so reaction abandoned.

Sources & evidence

ORD record
ord-4d540317a2f04c1c94f4d355d5594da0
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

Loading…