Stannous chloride dihydrate → 5-Bromo-2-(piperidin-1-yl)pyridin-3-amine

HRID 1431341ノート

反応式

HRID 1431341 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N+:14]([O-])=O)[C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.O.O.[Sn](Cl)Cl>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([NH2:14])[C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 61436Stannous chloride dihydrateHCID 467387925-Bromo-3-nitro-2-(piperidin-1-yl)pyridine

生成物 1

HCID 596314885-Bromo-2-(piperidin-1-yl)pyridin-3-amine

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

To a stirred mixture of 5-bromo-3-nitro-2-(piperidin-1-yl)pyridine (5.88 g, 20.5 mmol) in EtOAc (50 mL) was added tin(II) chloride dihydrate (23.5 g, 104 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 90° C. After 1 h, the reaction was cooled in an ice bath, then washed with 1M NaOH, water, and brine. After drying over anhydrous sodium sulfate and filtration, the organic solvent was removed under reduced pressure. The residue was purified with silica gel chromatography (0-15% EtOAc in hexanes) to provide a white solid as 5-bromo-2-(piperidin-1-yl)pyridin-3-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.57 (1H, d, J=2.2 Hz), 7.09 (1H, d, J=2.3 Hz), 5.04 (2H, s), 2.98 (4H, m), 1.73 (4H, m), 1.58 (2H, m).

後処理

  1. additionUpon complete addition of the reducing agent
  2. temperaturethe reaction was cooled in an ice bath
  3. washwashed with 1M NaOH, water, and brine
  4. dry with materialAfter drying over anhydrous sodium sulfate and filtration
  5. customthe organic solvent was removed under reduced pressure
  6. customThe residue was purified with silica gel chromatography (0-15% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-cb217b42873c4e26b36a07b85ef7d915
出典データセット
uspto-grants-2015_01
特許番号
US08940724B2

反応ノート

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