Dimethylamine → 5-bromo-N,N-dimethylpicolinamide

HRID 1643744Notes

Reaction equation

HRID 1643744 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[CH3:11][NH:12][CH3:13].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:12]([CH3:13])[CH3:11])=[O:10])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 6085445-Bromopyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 228316185-bromo-N,N-dimethylpicolinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-bromopyridine-2-carboxylic acid (1.5 g, 7.4 mmol), dimethyl amine (1.3 gm, 16 mmol), diisopropylethyl amine (excess) in DMF (10 mL) was added a solution of HATU in DMF (5 mL). After stirring the reaction for 14 hours at room temperature, the solvent was removed under reduced vacuum. The residue was taken up in ethyl acetate, washed with 1 N HCl (2x), brine (2×), 1 N NaOH (2×), brine (3×), dried over MgSO4, and concentrated. The crude was product was used in subsequent steps without further purification.

Workup

  1. customthe reaction for 14 hours at room temperature
  2. customthe solvent was removed under reduced vacuum
  3. washwashed with 1 N HCl (2x), brine (2×), 1 N NaOH (2×), brine (3×)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customwas used in subsequent steps without further purification

Sources & evidence

ORD record
ord-82e8b8a343e643fa9fa809aab10957d3
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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