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Sodium Hydroxide → 2-(1-(3-(1H-pyrazol-1-yl)phenyl)-3-methylbut-1-enyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1515954
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HRID 1515954 반응식
[N:1]1([C:6]2[CH:7]=[C:8]([C:12]([C:17]3[N:25](S(C4C=CC=CC=4)(=O)=O)[C:20]4=[N:21][CH:22]=[CH:23][CH:24]=[C:19]4[CH:18]=3)=[CH:13][CH:14]([CH3:16])[CH3:15])[CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[OH-].[Na+]>C(O)C.O1CCCC1>[N:1]1([C:6]2[CH:7]=[C:8]([C:12]([C:17]3[NH:25][C:20]4=[N:21][CH:22]=[CH:23][CH:24]=[C:19]4[CH:18]=3)=[CH:13][CH:14]([CH3:16])[CH3:15])[CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1
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5

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HCID 14798Sodium HydroxideHCID 672286202-(1-(3-(1H-pyrazol-1-yl)phenyl)-3-methylbut-1-enyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 672277872-(1-(3-(1H-pyrazol-1-yl)phenyl)-3-methylbut-1-enyl)-1H-pyrrolo[2,3-b]pyridine수율 69.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

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온도
85 °C

실험 절차

A solution of 2-(1-(3-(1H-pyrazol-1-yl)phenyl)-3-methylbut-1-enyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (3.4 g, 7.2 mmol) in ethanol (50 mL) and tetrahydrofuran (100 mL) was treated with an aqueous sodium hydroxide solution (10%, 20 mL). The reaction was stirred at 85° C. for 16 h. At this time, the reaction mixture was cooled to 25° C., concentrated in vacuo, diluted with water (100 mL) and then extracted with ethyl acetate (3×150 mL). The organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The resulting solid was washed with ethanol (15 mL), and dried to afford 2-(1-(3-(1H-pyrazol-1-yl)phenyl)-3-methylbut-1-enyl)-1H-pyrrolo[2,3-b]pyridine (1.64 g, 68.9%) as a white solid: 1H NMR (300 MHz, CDCl3) δ ppm 11.64 (s, 1H), 8.52 (d, 1H, J=2.1 Hz), 8.19 (dd, 1H, J1=4.5 Hz, J2=1.8 Hz), 7.95 (dd, 2H, J1=7.8 Hz, J2=1.2 Hz), 7.75-7.69 (m, 3H), 7.42 (t, 1H, J=8.1 Hz), 7.13-7.05 (m, 2H), 6.52 (t, 1H, J=2.1 Hz), 6.44 (d, 1H, J=1.8 Hz), 6.27 (d, 1H, J=9.9 Hz), 2.70-2.57 (m, 1H), 1.17 (s, 3H), 1.15 (s, 3H).

후처리

  1. temperatureAt this time, the reaction mixture was cooled to 25° C.
  2. concentrationconcentrated in vacuo
  3. additiondiluted with water (100 mL)
  4. extractionextracted with ethyl acetate (3×150 mL)
  5. washThe organic layers were washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washThe resulting solid was washed with ethanol (15 mL)
  10. customdried

출처 및 근거

ORD 기록
ord-7d52e21eeedd4d6b86d5aacd3353f3d7
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08222416B2

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