Hexane → HCID 18504805, compound

HRID 1357019Notes

Reaction equation

HRID 1357019 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCCCC.Br[C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[C:18]([CH2:29][C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[N:17][N:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>O1CCCC1.[Cl-].[Cl-].[Zn+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:28][O:27][C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][C:22]=1[O:25][CH3:26])[C:15]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[N:16][N:17]=[C:18]2[CH2:29][C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1

Participants

9

Reactant 5

HCID 8058HexaneHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 18504797HCID 18504797, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 18504805HCID 18504805, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In dry environment, ZnCl2 (379 mg, 2.78 mmoles) was dissolved in tetrahydrofuran (20 ml), then the temperature was brought to 0° C. and a 2M solution of phenyl lithium in hexane (1.4 ml, 2.8 mmoles) was dropped therein. The temperature was left to rise to room value and 1-bromo-6,7-dimethoxy-4-pyridin-4-ylmethyl-phthalazine (500 mg, 1.39 mmoles), obtained as described in example 65, palladium acetate (15 mg, 0.0695 mmole) and triphenylphosphine (36 mg, 0.139 mmole) were added and the whole was refluxed for 1.5 hour. The reaction was stopped with some drops of NaOH, then the mixture was dried and the residue taken up in water and CH2Cl2. The organic phase was dried to yield a residue which was chromatographed (eluent:methylene chloride, then methylene chloride/2% methanol, then methylene chloride/5% methanol). The eluate was dissolved in methylene chloride, treated with TONSIL® and filtered over celite. The mother liquor was dried yielding 172 mg of the title product.

Workup

  1. customwas brought to 0° C.
  2. waitThe temperature was left
  3. customobtained
  4. additionwere added
  5. temperaturethe whole was refluxed for 1.5 hour
  6. customthe mixture was dried
  7. customThe organic phase was dried
  8. customto yield a residue which
  9. customwas chromatographed (eluent
  10. dissolutionThe eluate was dissolved in methylene chloride
  11. additiontreated with TONSIL®
  12. filtrationfiltered over celite
  13. customThe mother liquor was dried

Sources & evidence

ORD record
ord-7926b270b7ca4e9393a98d9a2a209699
Source dataset
uspto-grants-2003_07
Patent number
US06589951B1

Reaction notes

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