Dimethylformamide → 2-{[(4-Chlorophenyl)sulfanyl](2,5-difluorophenyl)methyl}pyridine

HRID 2080376ノート

反応式

HRID 2080376 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9](O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.CN(C)C=O.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([SH:29])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>S(Cl)(Cl)=O.C(OCC)C>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([S:29][CH:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:25][CH:24]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 230286832-[(2,5-Difluorophenyl)-hydroxymethyl]pyridine

生成物 1

HCID 231148862-{[(4-Chlorophenyl)sulfanyl](2,5-difluorophenyl)methyl}pyridine収率 92%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 24386Thionyl Chloride溶媒

実験手順

The 2-[(2,5-difluorophenyl)-hydroxymethyl]pyridine (88 mg, 0.40 mmol) obtained in Referential Example 3 was dissolved in thionyl chloride (2.0 ml). To the resulting solution was added a catalytic amount of dimethylformamide, followed by stirring for 15 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added dioxane, and the resulting mixture was concentrated further. The residue was dissolved in dimethylformamide (5 ml). To the resulting solution were added 4-chlorobenzenethiol (79 mg, 0.55 mmol) and potassium carbonate (226 mg, 1.64 mmol) under a nitrogen atmosphere, and the 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 (128 mg, 92%) as an oil.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added dioxane
  3. concentrationthe resulting mixture was concentrated further
  4. dissolutionThe residue was dissolved in dimethylformamide (5 ml)
  5. stirringthe 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

出典と根拠

ORDレコード
ord-94c2df1bd7f3499d950d8bf29355d9e5
出典データセット
uspto-grants-2011_04
特許番号
US07932271B2

反応ノート

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