Morpholine → 5-Morpholinopyridin-3-amine

HRID 118

Reaction equation

HRID 118 reaction equation
C1COCCN1.Nc1cncc(Br)c1>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]>Nc1cncc(N2CCOCC2)c1

Participants

7

Reactant 2

HCID 8083MorpholineHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 583477375-Morpholinopyridin-3-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

Conditions

Temperature
150 °C

Procedure

diacetoxypalladium (20.76 mg, 0.09 mmol) was added to 5-bromopyridin-3-amine (160 mg, 0.92 mmol), morpholine (4028 µl, 46.24 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (64.2 mg, 0.11 mmol) and cesium carbonate (603 mg, 1.85 mmol). The resulting suspension was stirred at 150 °C for 30 minutes in a microwave. Reaction very messy but some product is visible. Reaction abandoned.

Sources & evidence

ORD record
ord-9c57f3e17c814398b6e1a1b710de4610
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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