Water → 3-Biphenyl-4-ylpyridin-2-amine

HRID 2035737Notes

Reaction equation

HRID 2035737 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=1.Br[C:23]1[C:24]([NH2:29])=[N:25][CH:26]=[CH:27][CH:28]=1.O>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:7]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]([C:23]2[C:24]([NH2:29])=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 8177002-Amino-3-bromopyridine

Product 1

HCID 654549503-Biphenyl-4-ylpyridin-2-amineYield 65.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2M aqueous sodium carbonate solution (6.64 ml), tetrakis(triphenylphosphine)palladium(0) (0.512 g), biphenyl-4-ylboronic acid (2.28 g) and 3-bromopyridin-2-amine (1.532 g) in dehydrated THF (30 mL) was heated under reflux overnight. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a solid. The obtained solid was crystallized from toluene, diisopropyl ether and acetonitrile to give the title compound (1.428 g) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a solid
  8. customThe obtained solid was crystallized from toluene, diisopropyl ether and acetonitrile

Sources & evidence

ORD record
ord-01ebf40fcc194b75bce6675de26f8591
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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