Ammonium Hydroxide → HCID 10402251, compound

HRID 374472Notes

Reaction equation

HRID 374472 reaction equation
[CH:1]1([C:7]#[CH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li]CCCC.FC(F)(F)S(O[C:20]1[CH:21]=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([O:30][CH3:31])=[C:25]([O:32][CH3:33])[CH:24]=2)(=O)=O.[NH4+].[OH-]>C1COCC1.C(Cl)(Cl)Cl.[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]1([C:7]#[C:8][C:20]2[CH:21]=[N:22][C:23]3[C:28]([CH:29]=2)=[CH:27][C:26]([O:30][CH3:31])=[C:25]([O:32][CH3:33])[CH:24]=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

9

Reactant 4

HCID 14923Ammonium HydroxideHCID 70263EthynylcyclohexaneHCID 10359684HCID 10359684, compoundHCID 178418339Butyllithium

Product 1

HCID 10402251HCID 10402251, compound

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

This reaction is carried out under anhydrous conditions. Cyclohexylacetylene (700 mg; 6.47 mmol) in 10 mL. THF is cooled to 0° C. To this is added 2.5M n-BuLi (3.0 mL; 7.44 mmol) and stirred for 30 min. at 0° C. under N2 atm and then 1.0M ZnCl2 (7.4 mL; 7.44 mmol). This is allowed to warm to room temperature and stirred for 3/4 hour. The reaction mixture is transferred via cannula to a flask containing 6,7-dimethoxyquinolin-3-yl trifluoromethane sulfonate (500 mg; 1.48 mmol) and Pd(PPh3)4 (83 mg; 0.074 mmol) in 4 mL of THF. This is then heated to 50° C. under N2 for 41/2 hours. The reaction mixture is then poured into 90 mL of 10% NH4OH, diluted with CHCl3 and stirred for 20 min. The aqueous layer is separated, and the organic layer washed with brine, dried over MgSO4, filtered, evaporated and chromatographed with 4:1 hexane: EtOAc to obtain 3-cyclohexylethynyl-6,7-dimethoxyquinoline, which is recrystallized from hexane, identified by NMR and used directly in the next step.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 3/4 hour
  3. customThe reaction mixture is transferred via cannula to a flask
  4. temperatureThis is then heated to 50° C. under N2 for 41/2 hours
  5. stirringstirred for 20 min
  6. customThe aqueous layer is separated
  7. washthe organic layer washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customchromatographed with 4:1 hexane

Sources & evidence

ORD record
ord-7ac63d9b42f64bf199e265d17711260d
Source dataset
uspto-grants-1996_01
Patent number
US05480883

Reaction notes

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