Sodium Carbonate → 5-(4-Chlorophenyl)pyridin-2-amine

HRID 1916545Notes

Reaction equation

HRID 1916545 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][N:9]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19](OB(O)O)=[CH:18][CH:17]=1>O1CCOCC1.CO.CCOC(C)=O.O>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:11]2[CH:12]=[CH:13][C:8]([NH2:7])=[N:9][CH:10]=2)=[CH:18][CH:17]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 706222-Amino-5-bromopyridineHCID 17810664p-Chlorophenylboric acid

Product 1

HCID 132426445-(4-Chlorophenyl)pyridin-2-amine

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

300 mL (600 mmol) of a 2 M Na2CO3 solution and 3.45 g (3.0 mmol) tetrakis-triphenylphosphane-palladium are added successively to a solution of 53.5 g (300 mmol) 2-amino-5-bromopyridine and 50.0 g (313 mmol) 4-chlorophenylboric acid in 1.0 L 1,4-dioxane and 250 mL methanol under argon. The reaction mixture is stirred for 2.5 h at 110° C. The solvent is eliminated i.vac., the residue is taken up in EtOAc and water. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH 20:1).

Workup

  1. dry with materialThe organic phase is dried over Na2SO4
  2. customFurther purification

Sources & evidence

ORD record
ord-95c0298ac78746789f541efddb200860
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

Loading…