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Benzylamine → N-Benzyl-4-chloropyridin-2-amine

HRID 427
Notes
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Reaction equation

HRID 427 reaction equation
Clc1ccnc(Cl)c1.NCc1ccccc1>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]>Clc1ccnc(NCc2ccccc2)c1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 7504BenzylamineHCID 335152,4-Dichloropyridine

Product 1

HCID 53419269N-Benzyl-4-chloropyridin-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 4144353

Conditions

Temperature
100 °C

Procedure

phenylmethanamine (0.111 mL, 1.01 mmol), 2,4-dichloropyridine (0.151 mL, 1.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (70.4 mg, 0.12 mmol) and cesium carbonate (660 mg, 2.03 mmol) were stirred in 1,4-dioxane (5 mL). The mixture was purged with nitrogen for 10 minutes. Palladium(II) acetate (22.76 mg, 0.10 mmol) was added and sealed into a microwave tube. The reaction was heated to 100 °C for 1 hour in the microwave reactor and cooled to RT. The reaction was heated to 100 °C for 1 hour in the microwave reactor and cooled to RT.

Sources & evidence

ORD record
ord-c8c1812487cb45a2983e445d322bb930
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
Palladium (II) acetate
Catalyst
HCID 312751,4-DioxaneSolvent