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

HRID 1908986

反応式

HRID 1908986 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[N:3]=1.O.[NH3:14]>>[NH2:14][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[N:3]=1

参加物

4

反応物 3

HCID 222Ammonia2 回HCID 962WaterHCID 70605292-Bromo-6-(1H-pyrazol-1-yl)pyridine

生成物 1

HCID 665204692-Amino-6-(1H-pyrazol-1-yl)pyridine収率 81%

実験手順

To a mixture of 2-bromo-6-(1H-pyrazol-1-yl)pyridine (3.0 mmol, 669 mg) and Cu2O (0.01 mmol, 1.0 mg) in glycol in autoclave NH3 was feed. The reaction was maintained under 10 atm of NH3 at 110° C. for 24 h. After cooling to room temperature, water was added and the aqueous phase 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=6:1 as eluent) to afford a white solid (388 mg, 81% yield). 1H NMR (400 MHz, CDCl3, ppm): 8.44 (s, 1H), 7.69 (s, 1H), 7.53 (m, 1H), 7.28 (m, 1H), 6.42-6.37 (m, 2H), 4.49 (br, 2H). 13C NMR (100 MHz, CDCl3, ppm): 151.45, 142.72, 140.73, 139.91, 127.58, 125.25, 110.89, 108.23.

後処理

  1. extractionthe aqueous phase was extracted with DCM
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customAfter solvent evaporation
  5. customthe crude product was purified by column chromatography on silica gel (Hexanes:ethyl acetate=6:1 as eluent)

出典と根拠

ORDレコード
ord-4fa80ff0e1c7418bb04267cf989f3656
出典データセット
uspto-grants-2013_12
特許番号
US08598351B2

関連ノート

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