Water → HCID 67487618、化合物

HRID 1523605ノート

反応式

HRID 1523605 の反応式
[CH3:1][C:2]1[C:3](=[S:8])[NH:4][CH:5]=[CH:6][CH:7]=1.Br[C:10]1[CH:11]=[C:12]([O:18][C:19]2[C:20]([CH3:25])=[N:21][CH:22]=[CH:23][CH:24]=2)[C:13]([C:16]#[N:17])=[N:14][CH:15]=1.[H-].[Na+].O>CN(C=O)C>[CH3:1][C:2]1[C:3]([S:8][C:10]2[CH:11]=[C:12]([O:18][C:19]3[C:20]([CH3:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[C:13]([C:16]#[N:17])=[N:14][CH:15]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 53714503-Methyl-2(1H)-pyridinethioneHCID 67485726HCID 67485726、化合物

生成物 1

HCID 67487618HCID 67487618、化合物収率 60.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

3-Methylpyridine-2(1H)-thione (0.906 g, 7.24 mmol) and 5-bromo-3-(2-methylpyridin-3-yloxy)picolinonitrile (2.00 g, 6.89 mmol) were dissolved in DMF (12 mL) and the mixture was cooled to 0° C. Sodium hydride (95%; 0.183 g, 7.24 mmol) was slowly added and the reaction was warmed to ambient temperature and stirred overnight. The reaction mixture was poured into water (100 mL), stirred for 30 minutes, then filtered to afford a solid which was purified over silica gel (2:3 hexanes:ethyl acetate). Concentration of the second UV active fraction to elute afforded 5-(3-methylpyridin-2-ylthio)-3-(2-methylpyridin-3-yloxy)picolinonitrile (1.40 g, 4.19 mmol, 60.7% yield) as a pale yellow/off white powder/crystals.

後処理

  1. temperaturethe reaction was warmed to ambient temperature
  2. stirringstirred for 30 minutes
  3. filtrationfiltered
  4. customto afford a solid which
  5. customwas purified over silica gel (2:3 hexanes:ethyl acetate)
  6. washConcentration of the second UV active fraction to elute

出典と根拠

ORDレコード
ord-5c1db53681604786bd1a55fcc74b9070
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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