Water → 5-Azidomethyl-2-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridine

HRID 2080400ノート

反応式

HRID 2080400 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18]O)=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl.CN(C)C=O.CCCCCC>[N:28]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])=[N:13][CH:14]=1)=[N+:29]=[N-:30]

参加物

8

反応物 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 230285882-[(4-Chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]-5-(hydroxymethyl)pyridine

生成物 1

HCID 231146355-Azidomethyl-2-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridine収率 49%

試薬・触媒・溶媒 3

HCID 5943Carbon Tetrachloride溶媒HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒

反応条件

温度
90 °C

実験手順

The 2-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-5-(hydroxymethyl)pyridine (471 mg, 1.15 mmol) obtained in Example 43 was dissolved in a mixture of carbon tetrachloride (4 ml) and N,N-dimethylformamide (16 ml). To the resulting solution were added sodium azide (112 mg, 1.72 mmol) and triphenylphosphine (451 mg, 1.72 mmol). The resulting mixture was stirred at 90° C. for 3 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed sequentially with water and brine. The resulting organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated under reduced pressure to give the title compound (244 mg, 0.561 mmol, 49%) as a colorless amorphous substance.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed sequentially with water and brine
  3. dry with materialThe resulting organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationethyl acetate=3:1 eluate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-4c29f3d11b144d0fa3b37dd1a480933f
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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