Cesium carbonate → 3-(4-chloropyridin-2-ylamino)-N-methylbenzamide

HRID 522916Notes

Reaction equation

HRID 522916 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.N[C:10]1[CH:19]=[CH:18][C:13]([C:14]([NH:16][CH3:17])=[O:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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.CC([N:75](C)C)=O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:75][C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:10]=2)[C:14]([NH:16][CH3:17])=[O:15])[CH:7]=1

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 335152,4-DichloropyridineHCID 2355164-Amino-N-methylbenzamideHCID 634876Binap, (A+-)-

Product 1

HCID 673535073-(4-chloropyridin-2-ylamino)-N-methylbenzamideYield 38%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

To a solution of 2, 4-dichloropyridine (0.500 g, 3.39 mmoL) and 4-amino-N-methylbenzamide (0.510 g, 3.39 mmoL) in dimethylacetamide (1 mL) was added cesium carbonate (1.6 g, 5.08 mmoL) and the reaction mixture was degassed for 15 min. Pd2(dba)3 (0.154 g, 0.169 mmol) and BINAP (105 mg, 0.169 mmol) were added and the reaction mixture was irradiated in the microwave at 120° C. for 1 h. Then reaction was quenched with water and extracted with EtOAc (2×50 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 3-((4-chloropyridin-2-yl)amino)-N-methylbenzamide (0.300 g, 38%) as a solid. Observed mass (M+1): 262.1

Workup

  1. customthe reaction mixture was degassed for 15 min
  2. customthe reaction mixture was irradiated in the microwave at 120° C. for 1 h
  3. customThen reaction
  4. customwas quenched with water
  5. extractionextracted with EtOAc (2×50 mL)
  6. washThe organic extracts were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-727d324dcc8f43dfa3ce010e92ead9f0
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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