Methyl iodide → methyl 4-[methyl(methylsulfonyl)amino]-1H-indole-6-carboxylate

HRID 14170

반응식

HRID 14170 반응식
[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)(=[O:4])=[O:3].[C:19](=O)([O-])[O-].[K+].[K+].IC>C1COCC1>[CH3:19][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[C:6]1[CH:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2

참가 물질

5

반응물 3

HCID 6328Methyl iodide2회HCID 11430Potassium CarbonateHCID 21086208Methyl 4-[(methylsulfonyl)amino]-1H-indole-6-carboxylate

생성물 1

HCID 21086207methyl 4-[methyl(methylsulfonyl)amino]-1H-indole-6-carboxylate수율 69.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of Methyl 4-[(methylsulfonyl)amino]-1H -indole-6-carboxylate (0.6 g) in THF (10 mL) was added potassium carbonate (0.309 g) and iodomethane (0.63 mL). The mixture was stirred at room temperature for 4 h then heated to 40° C. overnight. Iodomethane (0.3 mL) was added and the mixture heated an additional 3 h. The mixture was cooled to room temperature, partitioned between water and diethyl ether, dried over anhydrous sodium sulfate and concentrated. The residue was dissolved in ether and decolorizing carbon (2 g) was added and the mixture refluxed for 5 minutes then filtered through celite while hot. The ether was removed under reduced pressure to give 0.437 g of the title compound: MS (ESI+) for C12 H14 N2 O4 Si m/z 321.1 (M+K).

후처리

  1. temperaturethen heated to 40° C. overnight
  2. temperaturethe mixture heated an additional 3 h
  3. temperatureThe mixture was cooled to room temperature
  4. custompartitioned between water and diethyl ether
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in ether
  8. additionwas added
  9. temperaturethe mixture refluxed for 5 minutes
  10. filtrationthen filtered through celite while hot
  11. customThe ether was removed under reduced pressure

출처 및 근거

ORD 기록
ord-2d4556d0f71c4fc99fbb2155315f3880
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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