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Cyclobutanone → 1-(1-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-4-yl)cyclobutanol

HRID 2362720
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HRID 2362720 반응식
Br[C:2]1[CH:3]=[N:4][N:5]([C:7]2[C:12]([Cl:13])=[CH:11][N:10]=[C:9]3[N:14]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:15]([C:17]4[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=4)=[CH:16][C:8]=23)[CH:6]=1.C([Li])CCC.[C:36]1(=[O:40])[CH2:39][CH2:38][CH2:37]1>O1CCCC1>[Cl:13][C:12]1[C:7]([N:5]2[CH:6]=[C:2]([C:36]3([OH:40])[CH2:39][CH2:38][CH2:37]3)[CH:3]=[N:4]2)=[C:8]2[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=3)[N:14]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:9]2=[N:10][CH:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 14496CyclobutanoneHCID 67002903HCID 67002903, 화합물HCID 178418339Butyllithium

생성물 1

HCID 670038311-(1-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-4-yl)cyclobutanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A −78° C. solution of Example 113F (75 mgs, 0.148 mmol) in tetrahydrofuran (2.1 mL) was treated with n-butyllithium (2.45 M in hexanes, 0.121 mL, 0.295 mmol) dropwise over 3 minutes, and the reaction was stirred for 2 minutes. Cyclobutanone (0.022 mL, 0.295 mmol) was added, and the reaction was stirred for 1 hour at −78° C. The reaction was quenched by the addition of saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by flash chromatography on a silica gel column, eluting with a gradient of 0% to 4% methanol in dichloromethane, to provide the title compound. MS ESI(+) m/z 499.2 [M+H]+.

후처리

  1. stirringthe reaction was stirred for 1 hour at −78° C
  2. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate was purified by flash chromatography on a silica gel column
  9. washeluting with a gradient of 0% to 4% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-513b6a7664834835b99d33a7d0eaf75b
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691810B2

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