Sodium Chloride → HCID 11629897, compound

HRID 1821952Notes

Reaction equation

HRID 1821952 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2)=[O:9].[C:19](Cl)(=[O:21])[CH3:20].[Cl-].[Al+3].[Cl-].[Cl-].[Na+].[Cl-]>ClCCl.[Cl-].[Cl-].[Zn+2].O1CCCC1.C(OCC)(=O)C>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[C:19](=[O:21])[CH3:20])=[O:9]

Participants

10

Reactant 5

HCID 5234Sodium ChlorideHCID 6367Acetyl chlorideHCID 2737635methyl 1H-indole-5-carboxylateHCID 6451240Aluminum(III) ChlorideHCID 178418339Butyllithium

Product 1

HCID 11629897HCID 11629897, compound

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a three-neck flask, 4.20 ml (9.25 mmol) of a 2.2 M ZnCl2 solution in 20 ml absolute dichloromethane is charged under nitrogen and the solution is cooled to 0° C. using an ice bath. Thereafter, 5.62 ml (8.99 mmol) of a 1.6 M n-butyllithium solution are slowly added drop-wise. The reaction mixture is heated to room temperature, stirred for 1 hour, then admixed with the solution of 1.50 g (8.56 mmol) methylindole-5-carboxylate in 20 ml absolute dichloromethane and stirred again at room temperature for one hour. Thereafter, the batch is cooled to 0° C. and 1.28 ml (18.1 mmol) acetylchloride is carefully added so as to form an orange suspension. The latter is stirred at room temperature for 1 hour. Then, 0.93 g (7.02 mmol) aluminum chloride is added. After another hour of stirring at room temperature, hydrolysis with semi-saturated NaCl solution is carried out and 100 ml ethyl acetate and 20 ml tetrahydrofurane are added. Three extractions are carried out using ethyl acetate, the combined organic phases are washed with saturated NaCl solution and the organic phase is dried on sodium sulfate. The solvent is distilled off. Chromatographic purification of the residue on silica gel (flow agent: hexane/ethyl acetate 3:2) yields the product as a solid.

Workup

  1. temperatureThe reaction mixture is heated to room temperature
  2. stirringstirred again at room temperature for one hour
  3. temperatureThereafter, the batch is cooled to 0° C.
  4. customto form an orange suspension
  5. stirringThe latter is stirred at room temperature for 1 hour
  6. stirringAfter another hour of stirring at room temperature
  7. extractionThree extractions
  8. washthe combined organic phases are washed with saturated NaCl solution
  9. customthe organic phase is dried on sodium sulfate
  10. distillationThe solvent is distilled off
  11. customChromatographic purification of the residue on silica gel (flow agent: hexane/ethyl acetate 3:2)

Sources & evidence

ORD record
ord-44f3590149c34218ac757a198783d6ac
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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