Ammonium Chloride → 3-(2,6-Dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amine

HRID 1511025ノート

反応式

HRID 1511025 の反応式
Br[C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:11]([CH3:17])=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.C[Li].C([Li])CCC.N1C=CC=C(S[S:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)C=1.[NH4+].[Cl-]>C1COCC1>[CH3:17][C:11]1[C:10]([O:9][C:4]2[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([S:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)[CH:3]=2)=[CH:15][CH:14]=[C:13]([CH3:16])[N:12]=1

参加物

7

反応物 5

HCID 25517Ammonium ChlorideHCID 674861935-Bromo-3-(2,6-dimethylpyridin-3-yloxy)pyridin-2-amineHCID 866410882-(2-(Pyridin-3-yl)disulfanyl)pyridineHCID 178418339ButyllithiumHCID 178418348HCID 178418348、化合物

生成物 1

HCID 674868003-(2,6-Dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amine収率 63%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A 250 mL flask was charged with 5-bromo-3-(2,6-dimethylpyridin-3-yloxy)pyridin-2-amine (5.00 g, 17.66 mmol) and THF (100 mL) and purged with nitrogen. The solution was cooled to −78° C., methyl lithium (1.6 M in hexanes, 12.7 mL, 20.4 mmol) was added and the reaction was stirred for 5 minutes. Butyl lithium (2.5 M in Hexanes, 8.1 mL, 20.4 mmol) was added and the reaction was stirred for 10 minutes at −78° C. (solids formed). 2-(2-(Pyridin-3-yl)disulfanyl)pyridine (4.49 g, 20.4 mmol) was added and the reaction was warmed to ambient temperature and stirred for 18 hours. The reaction was poured into aqueous NH4Cl, extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified over silica gel (5% MeOH in CH2Cl2) to afford 3-(2,6-dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amine (3.5 g, 63%).

後処理

  1. custompurged with nitrogen
  2. stirringthe reaction was stirred for 10 minutes at −78° C.
  3. custom(solids formed)
  4. temperaturethe reaction was warmed to ambient temperature
  5. stirringstirred for 18 hours
  6. extractionextracted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified over silica gel (5% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-3f4eb5207beb4a6da70e6de5b19e77ef
出典データセット
uspto-grants-2012_07
特許番号
US08212045B2

反応ノート

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