2-Amino-3-bromo-5-methylpyridine → HCID 64129754, compound

HRID 2368031Notes

Reaction equation

HRID 2368031 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][C:16]=1[F:17]>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>[F:10][C:11]1[CH:12]=[C:13]([C:2]2[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=2)[CH:14]=[CH:15][C:16]=1[F:17]

Participants

6

Reactant 2

HCID 5193802-Amino-3-bromo-5-methylpyridineHCID 27343373,4-Difluorobenzeneboronic acid

Product 1

HCID 64129754HCID 64129754, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

3-Bromo-5-methylpyridin-2-amine (0.5 g, 2.7 mmol), 3,4-difluorophenylboronic acid (0.5 g, 3.2 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (0.1 g, 0.1 mmol) were dissolved in a mixture of dioxane (10 mL) and 1M aqueous sodium carbonate solution (8 mL) under argon and the mixture was heated to 100° C. for 1 hour. The reaction was diluted with ethyl acetate, separated and the organic layer was washed with brine, dried with sodium sulfate, filtered and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using n-heptane/ethyl acetate (v/v 1:1) as eluent. The title compound was obtained as a light brown crystalline solid (0.6 g, quant.).

Workup

  1. customseparated
  2. washthe organic layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-98e2179d8f64442facec7bf015ed0c6d
Source dataset
uspto-grants-2014_04
Patent number
US08703763B2

Reaction notes

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