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

HRID 1801498Notes

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]

Participants

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

customThe solvent was removed under reduced pressure
customThe residue obtained
filtrationfiltered through celite
washThe filtrate was washed with water (50 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
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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