5-Bromo-2-fluorotoluene → Methyl N-(4-fluoro-3-methylphenyl)piperidine-4-carboxylate

HRID 476

Reaction equation

HRID 476 reaction equation
COC(=O)C1CCNCC1.Cc1cc(Br)ccc1F>CC(C)(C)[O-].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].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>COC(=O)C1CCN(c2ccc(F)c(C)c2)CC1

Participants

7

Reactant 2

HCID 1235275-Bromo-2-fluorotolueneHCID 424914Methyl isonipecotate

Product 1

HCID 59023366Methyl N-(4-fluoro-3-methylphenyl)piperidine-4-carboxylateYield 0%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

In a 100 mL round-bottomed flask methyl piperidine-4-carboxylate (2.2 g, 15.36 mmol),4-bromo-1-fluoro-2-methylbenzene (1.954 mL, 15.36 mmol),Pd2(dba)3 (0.521 g, 0.57 mmol),BINAP (0.574 g, 0.92 mmol) and sodium tert-butoxide (4.43 g, 46.09 mmol) was taken in toluene (10 mL) under N2.The resulting reaction was stirred at 110 °C for 3 hrs. LCMS did not show product MS.Material was discrded.

Sources & evidence

ORD record
ord-498c0c75d66a47609408cbfbddaef8e5
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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