Hexane → 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-butan-1-ol

HRID 1515830

반응식

HRID 1515830 반응식
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[CH3:31][CH:32]([CH3:36])[CH2:33][CH:34]=[O:35]>O1CCCC1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[CH:34]([OH:35])[CH2:33][CH:32]([CH3:36])[CH3:31])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 8058HexaneHCID 115523-MethylbutanalHCID 242292371-Benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

생성물 1

HCID 672294341-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-butan-1-ol수율 71.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a suspension of 1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridine (10 g, 36.2 mmol) in dry tetrahydrofuran (400 mL) at −78° C. was added a n-butyllithium solution in n-hexane (2.5 M, 21.7 mL, 54.3 mmol) dropwise. The mixture was stirred at −78° C. for 30 min and then treated with 3-methyl-butyraldehyde (7 mL, 65.2 mmol) dropwise. The resulting mixture was stirred at −78° C. for 1 h and quenched with brine. The mixture was extracted with ethyl acetate (2×200 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash column chromatography (QingDao silica gel, 200-300 mesh, 20% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-butan-1-ol as a colorless oil (9.4 g, 71%): LC/MS m/e calcd for C20H22N2O4S [M+H]+ 363.43, observed 362.8.

후처리

  1. stirringThe resulting mixture was stirred at −78° C. for 1 h
  2. customquenched with brine
  3. extractionThe mixture was extracted with ethyl acetate (2×200 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography (QingDao silica gel, 200-300 mesh, 20% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-475ccb1c19d04898986435038cbc9f86
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222416B2

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