Triphenylphosphine → HCID 10192636, compound

HRID 1797103Notes

Reaction equation

HRID 1797103 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[CH:26]=[C:25]([NH2:27])[CH:24]=[CH:23][N:22]=1.C([Sn](CCCC)(CCCC)[CH:33]=[CH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)CCC>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:33](/[C:21]1[CH:26]=[C:25]([NH2:27])[CH:24]=[CH:23][N:22]=1)=[CH:34]\[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 3464554-Amino-2-bromopyridineHCID 4372073HCID 4372073, compound

Product 1

HCID 10192636HCID 10192636, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Under inert atmosphere (Ar) a mixture of palladium-(II)-acetate (0.117 mg, 0.5 mmol) and triphenylphosphine (0.248 g, 0.9 mmol) in DMF (13 ml) was stirred for 30 min at rt. 2-Bromo-pyridin-4-ylamine (0.90 g, 5.2 mmol) (H. J. den Hertog, C. R. Kolder and W. P. Combe, Rec. Trav. Chim., 1951, 70, 591) was added followed by tributyl-styryl-stannane (3.93 g, 10 mmol). After heating at 130° C. for 15 min the solvent was evaporated and the residue partitioned between AcOEt and 3N HCl. The aqueous phase was neutralized with 6N NaOH and extracted with AcOEt. The organic phase was dried with Na2SO4, concentrated and chromatographed (SiO2 with CH2Cl2/CH3OH/NH4OH=140/10/1) to give the title compound (0.40 g, 39%) as a colorless solid. Mp. 164–165° C. (AcOEt), MS: 196 (M+).

Workup

  1. temperatureAfter heating at 130° C. for 15 min the solvent
  2. customwas evaporated
  3. customthe residue partitioned between AcOEt and 3N HCl
  4. extractionextracted with AcOEt
  5. dry with materialThe organic phase was dried with Na2SO4
  6. concentrationconcentrated
  7. customchromatographed (SiO2 with CH2Cl2/CH3OH/NH4OH=140/10/1)

Sources & evidence

ORD record
ord-3120aeeadfad4aeb81979b6a17f2063a
Source dataset
uspto-grants-2006_04
Patent number
US07034044B2

Reaction notes

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