Triphenylphosphine → HCID 18504824, compound

HRID 1357018Notes

Reaction equation

HRID 1357018 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14]([CH2:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[N:13][N:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH4+].[Cl-]>O1CCCC1.C(OCC)(=O)C.[Cl-].[Cl-].[Zn+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14]([CH2:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[N:13][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 18504793HCID 18504793, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 18504824HCID 18504824, compoundYield 64.8%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

In anhydrous environment, ZnCl2 (863 mg, 6.33 mmoles) was dissolved in tetrahydrofuran (20 ml), and a 2M solution of benzyl magnesium chloride in tetrahydrofuran (3.2 ml, 2.5 equivalents) was dropped therein. After 30 minutes 1-chloro-6,7-dimethoxy-4-pyridin-4-ylmethyl-phthalazine (800 mg, 2.53 mmoles), obtained as described in example 63, palladium acetate (71 mg, 0.316 mmole) and triphenylphosphine (166 mg, 0.633 mmole) were added and the whole was refluxed. After 1 hour the mixture was poured into a saturated solution of NH4Cl and by adding ethyl acetate a solid precipitated. The whole was evaporated to dryness and the residue taken up in methylene chloride and extracted with concentrated ammonia. The organic phase was dried to yield a residue which was chromatographed (eluent:methylene chloride/2% methanol, then methylene chloride/5% methanol). The oily eluate was dissolved in methylene chloride and by adding HCl/ethyl ether a precipitate formed which was tritured in ethyl acetate and filtered to give 788 mg of the title product (yield: 64.8%).

Workup

  1. customobtained
  2. additionwere added
  3. temperaturethe whole was refluxed
  4. customprecipitated
  5. customThe whole was evaporated to dryness
  6. extractionextracted with concentrated ammonia
  7. customThe organic phase was dried
  8. customto yield a residue which
  9. customwas chromatographed (eluent
  10. dissolutionThe oily eluate was dissolved in methylene chloride
  11. additionby adding HCl/ethyl ether a precipitate
  12. customformed which
  13. filtrationfiltered

Sources & evidence

ORD record
ord-2d26f3e1f2fa460b87ba2a636a18bddf
Source dataset
uspto-grants-2003_07
Patent number
US06589951B1

Reaction notes

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