Sodium Carbonate → 5-Phenyl-2-pyridinamine

HRID 2054458Notes

Reaction equation

HRID 2054458 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:9]1([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 706222-Amino-5-bromopyridine

Product 1

HCID 1050975-Phenyl-2-pyridinamineYield 49.2%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5-bromopyridine (5.0 g, 28.90 mmol), phenylboronic acid (7.05 g, 57.80 mmol), dichlorobis(triphenylphosphine)palladium(II) (1.01 g, 1.45 mmol), and 2M Na2CO3(aq) (24 mL, 48 mmol) were combined in 150 mL of dimethoxyethane and heated to reflux for 1 hour. Upon cooling, the reaction mixture was diluted with EtOAc and washed with H2O and brine. The solvent was removed to give an amber oil which was chromatographed on silica gel eluting with hexanes/ethyl acetate (1:1) to afford 5-phenylpyridin-2-amine (2.42 g) as a tan solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureUpon cooling
  4. washwashed with H2O and brine
  5. customThe solvent was removed
  6. customto give an amber oil which
  7. customwas chromatographed on silica gel eluting with hexanes/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-88d7d5a6744946f9b003a819b6e9195e
Source dataset
uspto-grants-2008_02
Patent number
US07329678B2

Reaction notes

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