4-Pentyn-1-ol → HCID 18679547, compound

HRID 1633659Notes

Reaction equation

HRID 1633659 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13](OS(C(F)(F)F)(=O)=O)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[Li+].[Br-].[CH2:27]([OH:32])[CH2:28][CH2:29][C:30]#[CH:31]>N1CCCCC1.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:31]#[C:30][CH2:29][CH2:28][CH2:27][OH:32])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 793464-Pentyn-1-ol2×HCID 82050Lithium BromideHCID 86585588HCID 86585588, compound

Product 1

HCID 18679547HCID 18679547, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 11071931Dichloropalladium--(ethane-1,2-diyl)bis(diphenylphosphane) (1/1)CatalystHCID 8082PiperidineSolvent

Conditions

Temperature
60 °C

Procedure

To 8.4 g (20 mmol) Trifluoro-methanesulfonic acid 1-(4-bromo-phenyl)-1H-indol-5-yl ester in 30 ml piperidine were added 2.08 g (24 mmol) LiBr, 580 mg (0.05 eq) [1,2-Bis(diphenylphosphino)ethane]dichloropalladium(II) and 2.8 ml (30 mmol) 4-pentyn-1-ol. The mixture was stirred at 60° C. for 3 h, further 0.5 ml (5.4 mmol) 4-pentynol were added and stirred at 70° C. for 1 h. The reaction mixture was concentrated and dissolved in ether and water. 2M HCl was added and the inorganic phase was extracted with ether. The combined organic phases were washed with water and concentrated. The residue was dissolved in 50 ml EtOH and treated with 5 ml conc. NaOH at 50° C. for 30 min. The solution was concentrated and dissolved in water and ether. The organic phase was washed with water, dried over Na2SO4 and concentrated. Column chromatography with CH2Cl2 yielded 2.15 g (30%) 5-[1-(4-Bromo-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol as colorless viscous oil, MS: 353 (M, 1Br).

Workup

  1. stirringstirred at 70° C. for 1 h
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in ether
  4. addition2M HCl was added
  5. extractionthe inorganic phase was extracted with ether
  6. washThe combined organic phases were washed with water
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in 50 ml EtOH
  9. additiontreated with 5 ml conc. NaOH at 50° C. for 30 min
  10. concentrationThe solution was concentrated
  11. dissolutiondissolved in water
  12. washThe organic phase was washed with water
  13. dry with materialdried over Na2SO4
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-530ff9a2003e41618dd9b40dd8c2c4fa
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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