Pyrazole → 2-Bromo-6-(1H-pyrazol-1-yl)pyridine

HRID 1908985

반응식

HRID 1908985 반응식
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.CC([O-])(C)C.[K+].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Br)[N:14]=1>O1CCOCC1>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[N:14]=1

참가 물질

5

반응물 3

HCID 1048PyrazoleHCID 122742,6-DibromopyridineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 70605292-Bromo-6-(1H-pyrazol-1-yl)pyridine수율 90%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 1H-Pyrazole (10.0 mmol, 680 mg) in distilled dioxane (30 mL) were added KOtBu (11.0 mmol, 1.26 g), and followed by addition of 2,6-dibromopyridine (10.0 mmol, 2.37 g). The reaction mixture was refluxed for 48 hour, and then quenched with 5 mL of water. Solvent was removed under reduced pressure and water was added to the residue, then the mixture was extracted with DCM. The combined organic layers were washed with brine and dried over MgSO4. After solvent evaporation, the crude product was purified by column chromatography on silica gel (Hexanes:ethyl acetate=20:1 as eluent) to afford a white solid (2.01 g, 90%). 1H NMR (400 MHz, CDCl3, ppm): 8.53 (s, 1H), 7.92 (d, 1H, J=7.6 Hz), 7.73 (s, 1H), 7.67 (t, 1H, J=7.8 Hz), 7.35 (d, 1H, 7.6 Hz), 6.46 (s, 1H). 13C NMR (100 MHz, CDCl3, ppm): 162.72, 140.73, 139.91, 127.58, 125.25, 110.89, 108.23.

후처리

  1. temperatureThe reaction mixture was refluxed for 48 hour
  2. customquenched with 5 mL of water
  3. customSolvent was removed under reduced pressure and water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with DCM
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. customAfter solvent evaporation
  9. customthe crude product was purified by column chromatography on silica gel (Hexanes:ethyl acetate=20:1 as eluent)

출처 및 근거

ORD 기록
ord-95e63f97ec00497b9e4dd19c82b313a5
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598351B2

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