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

HRID 1396444

反応式

HRID 1396444 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
160 °C

実験手順

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].

後処理

  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)

出典と根拠

ORDレコード
ord-a3cd4cc96feb4bd681392ab239d08faa
出典データセット
uspto-grants-2014_12
特許番号
US08901124B2

関連ノート

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