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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
ノート
印刷プレビュー

反応式

HRID 2362720 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 14496CyclobutanoneHCID 67002903HCID 67002903、化合物HCID 178418339Butyllithium

生成物 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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-513b6a7664834835b99d33a7d0eaf75b
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08691810B2

反応ノート

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