Potassium Carbonate → N-(5-bromo-3-methyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamide

HRID 1916741

Reaction equation

HRID 1916741 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:6][C:7]1[CH:8]=[C:9]([CH3:18])[C:10]([NH:13][C:14](=[O:17])[CH2:15]Cl)=[N:11][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:6][C:7]1[CH:8]=[C:9]([CH3:18])[C:10]([NH:13][C:14](=[O:17])[CH2:15][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:11][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 52228026n-(5-Bromo-3-methyl-pyridin-2-yl)-2-chloro-acetamide

Product 1

HCID 67362705N-(5-bromo-3-methyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.81 mL (9.9 mmol) pyrrolidine are added to a suspension of 2.37 g (9.0 mmol) N-(5-bromo-3-methyl-pyridin-2-yl)-2-chloro-acetamide and 2.49 g (18 mmol) K2CO3 in 22.5 mL DMF and the reaction mixture is stirred for 20 h at RT. It is diluted with water, extracted exhaustively with EtOAc, the combined organic phases are washed with water and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is taken up in a little diisopropylether, cooled to 0° C., the crystals precipitated are suction filtered and dried in the air.

Workup

  1. extractionextracted exhaustively with EtOAc
  2. washthe combined organic phases are washed with water
  3. dry with materialdried over Na2SO4
  4. temperaturecooled to 0° C.
  5. customthe crystals precipitated
  6. filtrationare suction filtered
  7. customdried in the air

Sources & evidence

ORD record
ord-c0b803486c1f41659abfeb3b7564a30c
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Linked notes

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