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

HRID 534010노트

반응식

HRID 534010 반응식
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

참가 물질

7

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-30bd9a271df84625a35b0387d5e726e3
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853409B2

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