2-Fluoro-5-methylpyridine → N-(4-(3-bromopyridin-2-yloxy)phenyl)-5-methylpyridin-2-amine

HRID 473629Notes

Reaction equation

HRID 473629 reaction equation
[Br:1][C:2]1[C:3]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.F[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=1>CN1C(=O)CCC1.O>[Br:1][C:2]1[C:3]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH:13][C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 27746352-Fluoro-5-methylpyridineHCID 577562564-(3-Bromopyridin-2-yloxy)benzenamine

Product 1

HCID 59374189N-(4-(3-bromopyridin-2-yloxy)phenyl)-5-methylpyridin-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

To a pressure vessel was added 4-(3-bromopyridin-2-yloxy)aniline (7.23 g, 27.3 mmol) and 2-fluoro-5-methylpyridine (3.03 mL, 27.2 mmol) in NMP (13.61 mL) to stir at 170° C. Upon completion, the reaction mixture was diluted with water and extracted with EtOAc. The organic extract was washed with water, sat NaCl, dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed to provide N-(4-(3-bromopyridin-2-yloxy)phenyl)-5-methylpyridin-2-amine.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-9885f166e218438e8b457acebbf4f82e
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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