Diethyl Ether → 2-{[(4-Chlorophenyl)sulfanyl](2,5-difluorophenyl)methyl}-3-methoxypyridine

HRID 2080379노트

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HRID 2080379 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9](O)[C:10]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][N:11]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>S(Cl)(Cl)=O.CN(C)C=O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26][CH:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:22][CH:21]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 23114591HCID 23114591, 화합물

생성물 1

HCID 231146722-{[(4-Chlorophenyl)sulfanyl](2,5-difluorophenyl)methyl}-3-methoxypyridine수율 67.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 24386Thionyl Chloride용매

실험 절차

After the 2-[(2,5-difluorophenyl)-hydroxymethyl]-3-methoxypyridine (251 mg, 1.0 mmol) obtained in Referential Example 9 was dissolved in thionyl chloride (2.0 ml), a catalytic amount of dimethylformamide was added to the resulting solution. The resulting mixture was stirred for 16 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added dioxane, followed by further concentration. The residue thus obtained was dissolved in dimethylformamide (10 ml). To the resulting solution were added 4-chlorobenzenethiol (289 mg, 2.0 mmol) and potassium carbonate (1.10 g, 8.0 mmol) under a nitrogen atmosphere. The resulting mixture was stirred at 50° C. for 1 hour. After the reaction mixture was cooled to room temperature, diethyl ether (50 ml) was added thereto. The resulting mixture was washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (hexane:ethyl acetate=10:1) to give the title compound (256 mg, 58%) as an oil.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added dioxane
  3. concentrationfollowed by further concentration
  4. customThe residue thus obtained
  5. stirringThe resulting mixture was stirred at 50° C. for 1 hour
  6. washThe resulting mixture was washed with water and brine
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-85067ee309334df99db1ad667663ba37
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932271B2

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