3-Bromopyridine → tert-butyl (3R)-3-methyl-4-pyridin-3-ylpiperazine-1-carboxylate

HRID 512

Reaction equation

HRID 512 reaction equation
Brc1cccnc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>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]>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1cccnc1

Participants

7

Reactant 2

HCID 122863-BromopyridineHCID 2756811(R)-1-Boc-3-methylpiperazine

Product 1

HCID 89555981tert-butyl (3R)-3-methyl-4-pyridin-3-ylpiperazine-1-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
85 °C

Procedure

TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.145 g, 0.16 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.183 g, 0.32 mmol) were added to a mixture of Sodium tert-butoxide (0.912 g, 9.49 mmol), 3-bromopyridine (0.610 mL, 6.33 mmol),(R)-tert-butyl 3-methylpiperazine-1-carboxylate (1.901 g, 9.49 mmol) and toluene (20 mL) under nitrogen. The mixture was heated at 85 °C for 16 hours before being cooled to RT and filtered through celite. The filtrate was concentrated and the reaction mixture was seperated by flash silica chromatography, elution gradient 20 to 40% EtOAc in heptane. No product was isolated. .

Sources & evidence

ORD record
ord-d7d7e0dc4c0741f08ecfdb907acad13f
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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