Potassium Carbonate → HCID 18797034, compound

HRID 1003709Notes

Reaction equation

HRID 1003709 reaction equation
[C:1]1([C:7]2[CH:37]=[CH:36][C:10]([C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:27][CH2:26][C:25]4[C:20](=[CH:21][C:22](OS(C(F)(F)F)(=O)=O)=[CH:23][CH:24]=4)[CH2:19]3)=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:38]([O:40]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:39].[Cl-].[Li+].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.Cl.O>[C:38]([C:22]1[CH:21]=[C:20]2[C:25]([CH2:26][CH2:27][N:18]([CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:11](=[O:12])[C:10]3[CH:9]=[CH:8][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:37][CH:36]=3)[CH2:19]2)=[CH:24][CH:23]=1)(=[O:40])[CH3:39]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 18797049HCID 18797049, compound

Product 1

HCID 18797034HCID 18797034, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(4-(4-Phenylbenzoylamino)butyl)-7-trifluoromethylsulfonyloxy-1,2,3,4-tetrahydroisoquinoline (0.515 g, 0.97 mmol), (1-ethoxyvinyl)tributyltin (0.420 g, 1.16 mmol), lithium chloride (0.121 g, 2.85 mmol) and tetrakis-(triphenylphosphine)palladium (0) (0.057 g, 0.05 mmol) in 1,4-dioxane (15 ml) were heated at reflux under argon for 16 h. The cooled reaction mixture was treated with water (2.0 ml) and aqueous 5N hydrogen chloride (4 drops), then stirred at room temperature for 0.5 h. The resulting solution was poured onto saturated, aqueous potassium carbonate (20 ml) and the product was extracted with ethyl acetate (2×25 ml). The combined organic extracts were washed with brine (40 ml), dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica using 50-100% ethyl acetate--pentane gradient elution to afford the title compound as a colourless solid (0.210 g, 51%).

Workup

  1. temperatureat reflux under argon for 16 h
  2. customThe cooled reaction mixture
  3. extractionthe product was extracted with ethyl acetate (2×25 ml)
  4. washThe combined organic extracts were washed with brine (40 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica using 50-100% ethyl acetate
  8. washpentane gradient elution

Sources & evidence

ORD record
ord-8e1661ae308949799a2d5876a70da116
Source dataset
uspto-grants-2000_04
Patent number
US06046210

Reaction notes

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