Water → 2-(2-Furanyl)-5-methanesulfonylindole

HRID 1432226

반응식

HRID 1432226 반응식
C1(S([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:12]=2I)(=O)=O)C=CC=CC=1.C(N(CC)CC)C.[C:29]([C:31]1[O:32][CH:33]=[CH:34][CH:35]=1)#[CH:30].O>CN(C)C=O>[O:32]1[CH:33]=[CH:34][CH:35]=[C:31]1[C:29]1[NH:10][C:11]2[C:12]([CH:30]=1)=[CH:13][C:14]([S:17]([CH3:20])(=[O:18])=[O:19])=[CH:15][CH:16]=2

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 140409Furan, 2-ethynyl-HCID 225043761-Benzenesulfonylamino-2-iodo-4-methanesulfonylbenzene

생성물 1

HCID 225044472-(2-Furanyl)-5-methanesulfonylindole수율 29.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
60 °C

실험 절차

To a suspension of the compound obtained in Example 8 (5) (2.00 g), bistriphenylphosphine palladium dichloride (321 mg), cuprous iodide (87.0 mg) and triethylamine (1.38 g) in N,N-dimethylformamide (46 ml), a solution of 2-ethynylfuran (842 mg) in N,N-dimethylformamide (46 ml) was slowly added dropwise under nitrogen atmosphere and the mixture was stirred at 60° C. for 3 hours. The reaction solution was then poured into water, extracted with chloroform, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (methanol:chloroform=1:100). To a solution of the obtained colorless amorphous compound (1.10 g) in methanol (28 ml) was added a 1N aqueous potassium hydroxide solution (5.52 ml) and the mixture was stirred at 60° C. for 1 hour. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The resulting residue was poured into water, extracted with chloroform, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (methanol chloroform=1:20) to obtain 350 mg of the desired product as a brown crystal.

후처리

  1. extractionextracted with chloroform
  2. washwashed with a saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was separated
  7. additionTo a solution of the obtained colorless amorphous compound (1.10 g) in methanol (28 ml) was added a 1N aqueous potassium hydroxide solution (5.52 ml)
  8. stirringthe mixture was stirred at 60° C. for 1 hour
  9. customAfter completion of the reaction
  10. concentrationthe reaction solution was concentrated under reduced pressure
  11. additionThe resulting residue was poured into water
  12. extractionextracted with chloroform
  13. washwashed with a saturated aqueous NaCl solution
  14. dry with materialdried over anhydrous sodium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated under reduced pressure
  17. customThe resulting residue was separated

출처 및 근거

ORD 기록
ord-626deb9df2e84658842ac908543ebf04
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612070B2

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