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Sodium hydride → N,N-dimethyl-2-((4-methylpyridin-3-yl)amino)benzamide

HRID 1801498
Notes
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Reaction equation

HRID 1801498 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].Cl[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH3:20].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[H-].[Na+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl>[CH3:7][N:6]([CH3:8])[C:4](=[O:5])[C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[NH:1][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH3:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 634876Binap, (A+-)-HCID 27629253-Chloro-4-methylpyridineHCID 47781752-Amino-N,N-dimethylbenzamide

Product 1

HCID 59506321N,N-dimethyl-2-((4-methylpyridin-3-yl)amino)benzamideYield 26%

Reagents, catalysts & solvents 3

HCID 167845
palladium(II) acetate
Catalyst
HCID 6344DichloromethaneSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-amino-N,N-dimethylbenzamide (1.3 g, 6.77 mmol), 3-chloro-4-methylpyridine (0.745 mL, 6.77 mmol), Palladium acetate (0.150 g) and BINAP (0.60 g) in 1,4-dioxane (10 mL) was added NaH (0.677 g, 16.93 mmol) and the resulting mixture was heated at 100° C. for 2 hours. The solvent was removed under reduced pressure. The residue obtained was taken into dichloromethane (50 mL) and filtered through celite. The filtrate was washed with water (50 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified using flash column chromatography (SiO2) to provide 0.450 g of the desired product as a dark oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue obtained
  3. filtrationfiltered through celite
  4. washThe filtrate was washed with water (50 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-3c4ae5cdd3ce4122b77079efb1097140
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08349827B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes