Methyl iodide → HCID 18962034, compound

HRID 1707694Notes

Reaction equation

HRID 1707694 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I>CC(N(C)C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH3:24])[C:9]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5133930Ethyl 3-(4-fluorophenyl)-1H-indole-2-carboxylate

Product 1

HCID 18962034HCID 18962034, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 8.0 g. (28 mmol.) of ethyl 3-(4'-fluorophenyl)indole-2-carboxylate in 30 ml. of dry dimethylacetamide stirred under nitrogen at -10° C., 1.6 g. (33 mmol.) of sodium hydride is added. The reaction mixture is stirred at -10° C. under nitrogen for 45 min., 4.8 g. (32 mmol.) of methyl iodide is added at -10° C., and the reaction mixture is allowed to warm to room temperature and stirred under nitrogen at room temperature for 2 hrs. The reaction mixture is poured into 400 ml. of ice/water, neutralized with 4 ml. of 2N. hydrochloric acid and extracted several times with diethyl ether. The diethyl ether extracts are combined, washed with water, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated at reduced pressure. The residue is purified by column chromatography utilizing a silica gel column and chloroform as the eluant. The fractions containing the product are combined and evaporated at reduced pressure, and the residue is crystallized from n-hexane/petroleum ether to obtain the product (7.6 g. (91%)), m.p. 61°-62° C.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred under nitrogen at room temperature for 2 hrs
  3. additionThe reaction mixture is poured into 400 ml
  4. extractionhydrochloric acid and extracted several times with diethyl ether
  5. washwashed with water
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated at reduced pressure
  10. customThe residue is purified by column chromatography
  11. additionThe fractions containing the product
  12. customevaporated at reduced pressure
  13. customthe residue is crystallized from n-hexane/petroleum ether
  14. customto obtain the product (7.6 g. (91%)), m.p. 61°-62° C.

Sources & evidence

ORD record
ord-3236ddce62764a7693386d3c9f074f6f
Source dataset
uspto-grants-1994_10
Patent number
US05354772

Reaction notes

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