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Potassium Phosphate, Tribasic → 2-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide

HRID 62483
Notes
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Reaction equation

HRID 62483 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([NH:15][CH3:16])=[O:14].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:7]=[C:6]([NH:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([NH:15][CH3:16])=[O:14])[C:5]([Cl:9])=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 3080722-Amino-N-methylbenzamideHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 534009652,5-Dichloro-4-iodopyridine

Product 1

HCID 575168912-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamideYield 56.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A 150-mL sealed tube was charged with 2,5-dichloro-4-iodopyridine (3.5 g, 12.78 mmol), 2-amino-N-methylbenzamide (1.919 g, 12.78 mmol) and tripotassium phosphate (8.14 g, 38.3 mmol) in 1,4-dioxane (100 mL). The reaction mixture was degassed with nitrogen for 10 min. Bis(2-diphenylphosphinophenyl)ether (DPEPhos, 0.688 g, 1.278 mmol) and Pd(OAc)2 (0.115 g, 0.511 mmol) were added and the reaction mixture was heated in a 120° C. oil bath over night. The reaction mixture was filtered through celite, which was washed with dioxane. The solvent was evaporated to dryness and the solid was washed with EtOH (10 mL×3) to give 2.14 g (56%) of product as an off white solid.

Workup

  1. customA 150-mL sealed tube
  2. customThe reaction mixture was degassed with nitrogen for 10 min
  3. filtrationThe reaction mixture was filtered through celite, which
  4. washwas washed with dioxane
  5. customThe solvent was evaporated to dryness
  6. washthe solid was washed with EtOH (10 mL×3)

Sources & evidence

ORD record
ord-63006ffb9bab4ecca372336ff57f1a83
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09446034B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes