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

HRID 1396444

반응식

HRID 1396444 반응식
C([N:8](C(OC(C)(C)C)=O)[C:9]1[N:14]=[C:13](Br)[CH:12]=[CH:11][CH:10]=1)(OC(C)(C)C)=O.[OH-].[K+].[NH:25]1[CH:29]=[CH:28][CH:27]=[N:26]1>CCOC(C)=O.[Cu]>[N:25]1([C:13]2[N:14]=[C:9]([NH2:8])[CH:10]=[CH:11][CH:12]=2)[CH:29]=[CH:28][CH:27]=[N:26]1

참가 물질

6

반응물 3

HCID 1048PyrazoleHCID 14797Potassium HydroxideHCID 162179716-(Di-Boc-amino)-2-bromopyridine

생성물 1

HCID 665204692-Amino-6-(1H-pyrazol-1-yl)pyridine수율 85.1%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
160 °C

실험 절차

6-(Di-Boc-amino)-2-bromopyridine (1.0 g, 2.68 mmol, ChronTech), copper (341 mg, 5.36 mmol), potassium hydroxide (301 mg, 5.36 mmol), and 1H-pyrazole (1.82 g, 26.8 mmol, Eq: 10) were combined and stirred at 160° C. for 18 h. The reaction mixture was cooled, diluted with EtOAc (50 mL) and the solids removed by filtration. The dark blue filtrate was washed with saturated aqueous NaHCO3 and brine then concentrated onto silica gel and purified by chromatography (40 g RediSep column, 20 to 100% ethyl acetate in hexanes, 20 min) to give 6-(1H-pyrazol-1-yl)pyridin-2-amine (365 mg, 2.28 mmol, 85%) as a white solid. MS (EI/CI) m/z: 161.2 [M+H].

후처리

  1. temperatureThe reaction mixture was cooled
  2. customthe solids removed by filtration
  3. washThe dark blue filtrate was washed with saturated aqueous NaHCO3 and brine
  4. concentrationthen concentrated onto silica gel
  5. custompurified by chromatography (40 g RediSep column, 20 to 100% ethyl acetate in hexanes, 20 min)

출처 및 근거

ORD 기록
ord-a3cd4cc96feb4bd681392ab239d08faa
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901124B2

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