Triphenylphosphine → HCID 11816425, compound

HRID 1797102Notes

Reaction equation

HRID 1797102 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][N:22]=1.C([Sn](CCCC)(CCCC)[CH:35]=[CH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)CCC>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:35](/[C:21]1[N:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=1)=[CH:36]\[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 783082-Chloro-5-nitropyridineHCID 4372073HCID 4372073, compound

Product 1

HCID 11816425HCID 11816425, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Under inert atmosphere (Ar) a mixture of palladium(II)-acetate (0.45 g, 2 mmol) and triphenylphosphine (0.95 g, 3.6 mmol) in DMF (50 ml) was stirred for 0.5 hr at rt. Then 2-chloro-5-nitropyridine (3.2 g, 20 mmol) and tributyl-styryl-stannane (15.7 g, 40 mmol) was added and the mixture was stirred at 130° C. for 15 hr. The solvent was evaporated and the residue partitioned between AcOEt and 1N 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=97/3) to give the title compound (0.90 g, 23%) as a yellow solid. Mp. 159–160° C. (AcOEt), MS: 196 (M+).

Workup

  1. stirringthe mixture was stirred at 130° C. for 15 hr
  2. customThe solvent was evaporated
  3. customthe residue partitioned between AcOEt and 1N HCl
  4. extractionextracted with AcOEt
  5. dry with materialThe organic phase was dried with Na2SO4
  6. concentrationconcentrated
  7. customchromatographed (SiO2 with CH2Cl2/CH3OH=97/3)

Sources & evidence

ORD record
ord-77604f352bed437088fb9c2d79c90ed1
Source dataset
uspto-grants-2006_04
Patent number
US07034044B2

Reaction notes

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