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2-Amino-N-methylbenzamide → 2-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide

HRID 28
Notes
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Reaction equation

HRID 28 reaction equation
CNC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1>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]>CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 3080722-Amino-N-methylbenzamideHCID 534009652,5-Dichloro-4-iodopyridine

Product 1

HCID 575168912-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamideYield 69.36%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
100 °C

Procedure

2-amino-N-methylbenzamide (110 mg, 0.73 mmol), 2,5-dichloro-4-iodopyridine (200 mg, 0.73 mmol), diacetoxypalladium (8.20 mg, 0.04 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (42.3 mg, 0.07 mmol) and cesium carbonate (357 mg, 1.10 mmol) suspended in 1,4-dioxane (4 mL) was weighed out in a microwave vial and sealed. argon was let to bubble into the mixture for 5 minutes at rt then the resulting mixture was stirred at 100 °C for 1 hour. The reaction mixture was allowed to cool to room temperature under stirring and diluted with dichloromethane. Insolubles were removed by filtration and the filtrate was concentrated. The residue was triturated in DCM, collected by filtration and dried to afford 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (150 mg, 69.4 %) as a off- white solid.

Sources & evidence

ORD record
ord-b94a4cbc1fbd4100843834a92096e35b
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes