2,6-Dibromopyridine → 6-Bromo-N-(tetrahydro-2H-pyran-4-yl)pyridin-2-amine

HRID 727

Reaction equation

HRID 727 reaction equation
Brc1cccc(Br)n1.NC1CCOCC1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>Brc1cccc(NC2CCOCC2)n1

Participants

7

Reactant 2

HCID 122742,6-DibromopyridineHCID 4192234-Aminotetrahydropyran

Product 1

HCID 639627976-Bromo-N-(tetrahydro-2H-pyran-4-yl)pyridin-2-amineYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 4144353Palladium (II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

to 2,6-dibromopyridine (100 mg, 0.42 mmol), 4-Aminotetrahydropyran (42.7 mg, 0.42 mmol) in dioxane (3 mL) while bubbling N2 was added Xantphos (24.43 mg, 0.04 mmol), CS2CO3 (316 mg, 0.97 mmol) and palladium(II) acetate (9.48 mg, 0.04 mmol). This was heated in a microwave at 130 oC for 30 mins. A small peak corresponding to product was obseved. Discontinued

Sources & evidence

ORD record
ord-13cef69f8e724020954e5476c0d66794
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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