Triethylamine → 5-bromo-N,N-dimethylpicolinamide

HRID 1643607Notes

Reaction equation

HRID 1643607 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.Cl.[CH3:12][NH:13][CH3:14].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:12][N:13]([CH3:14])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[O:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 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-dimethylpicolinamideYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromopyridine-2-caboxylic acid (3.00 g, 14.85 mmol), dimethyl amine hydrochloride (1.82 g, 22.30 mmol) and triethylamine (6.21 ml, 44.60 mmol) in 20 mL of DMF was added HATU (8.47 g, 22.30 mmol). The mixture was stirred at room temperature overnight, quenched with water, extracted with 3×EtOAc. The combined organic layer was washed with 2×H2O, dried with Na2SO4, concentrated and purified by Biotage column chromatography with 60-70% EtOAc in hexanes to give a yellow oil (1.56 g, 46% yield). 1H NMR (400 MHz, CDCl3) δ 8.59 (d, J=1.77 Hz, 1 H) 7.88 (dd, J=8.34, 2.27 Hz, 1 H) 7.52 (d, J=8.34 Hz, 1 H) 3.06 (d, J=14.15 Hz, 6 H); LCMS for C8H9BrN2O m/z 229.00 (M+H+).

Workup

  1. customquenched with water
  2. extractionextracted with 3×EtOAc
  3. washThe combined organic layer was washed with 2×H2O
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. custompurified by Biotage column chromatography with 60-70% EtOAc in hexanes

Sources & evidence

ORD record
ord-07723f64036941789fadd09d2380deea
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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