Diisopropylethylamine → 4-bromo-N-(4-isopropyl-3-methylphenyl)picolinamide

HRID 2283474Notes

Reaction equation

HRID 2283474 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10]C)=O)[CH:3]=1.Cl.[CH:13]([C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[CH3:23])([CH3:15])[CH3:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([CH:13]([CH3:14])[CH3:15])=[C:17]([CH3:23])[CH:18]=2)=[O:10])[CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27962704-Isopropyl-m-toluidinium chlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12828947Methyl 4-bromopicolinate

Product 1

HCID 1182507534-bromo-N-(4-isopropyl-3-methylphenyl)picolinamideYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-bromopicolinate (1.0 g, 5.0 mmol) in DCM (500 mL) and DMF (20 mL) was added 4-isopropyl-3-methylbenzenamine hydrochloride (1.08 g, 5.90 mmol), HATU (3.8 g, 10 mmol), DIPEA (4.9 mL, 30 mmol) and the mixture was stirred at reflux overnight. After cooling to room temperature and evaporation of the solvent, the residue was purified by combi-flash (ISCO, 40g silica, UV254, 3:1 pet ether/ethyl acetate) to afford 4-bromo-N-(4-isopropyl-3-methylphenyl)picolinamide (1.32 g, 80% yield) as a yellow oil: MS (ES) m/z 333 (M+H).

Workup

  1. temperatureat reflux overnight
  2. customevaporation of the solvent
  3. customthe residue was purified by combi-flash (ISCO, 40g silica, UV254, 3:1 pet ether/ethyl acetate)

Sources & evidence

ORD record
ord-f777dd1fb7934bd5871f4b96b378eeb3
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

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