Sodium hydride → HCID 67485570、化合物

HRID 1523577ノート

反応式

HRID 1523577 の反応式
[CH2:1]([C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].[H-].[Na+].Br[C:13]1[CH:14]=[C:15]([N+]([O-])=O)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[SH:30]>CN(C=O)C.O>[CH2:1]([C:3]1[C:8]([O:9][C:15]2[C:16]([C:19]#[N:20])=[N:17][CH:18]=[C:13]([S:30][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=3)[CH:14]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

参加物

7

反応物 4

HCID 24758Sodium hydride2 回HCID 27696985-Bromo-3-nitropyridine-2-carbonitrileHCID 38372322-Ethylpyridin-3-olHCID 178418616HCID 178418616、化合物

生成物 1

HCID 67485570HCID 67485570、化合物収率 58%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-ethylpyridin-3-ol (2.5 g, 20.3 mmol) in DMF (20 ml) at 0° C. was added sodium hydride (0.512 g, 21.3 mmol). After 15 minutes, 5-bromo-3-nitropicolinonitrile (4.63 g, 20.3 mmol) was added and the mixture was allowed to warm slowly to ambient temperature and stirred for 2 hours. Pridine-2-thiol (0.804 g, 7.23 mmol) was added followed by sodium hydride (0.182 g, 7.60 mmol) and the mixture was stirred at ambient temperature overnight. Water (200 ml) was added and the mixture was extracted with diethyl ether (3×100 mL), washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified over silica gel (25 to 75% EtOAc in Hexanes) to afford 3-(2-ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile (1.4 g, 4.19 mmol).

後処理

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. extractionthe mixture was extracted with diethyl ether (3×100 mL)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified over silica gel (25 to 75% EtOAc in Hexanes)

出典と根拠

ORDレコード
ord-3e235affd4ce4944b0574356f658e632
出典データセット
uspto-grants-2015_07
特許番号
US09079890B2

反応ノート

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