Dimethylamine → 5-bromo-N,N-dimethylpicolinamide

HRID 1177271Notes

Reaction equation

HRID 1177271 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 (2×), 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 (2×), 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-76449272b51c458a9736354396e6c4f3
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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