Phosphorus oxychloride → HCID 86640732、化合物

HRID 529425ノート

反応式

HRID 529425 の反応式
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[C:8]([F:14])=[N+:9]([O-])[CH:10]=[CH:11][CH:12]=2)=[C:4]([C:17](=[O:23])[N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:3]=1.P(Cl)(Cl)([Cl:26])=O>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[C:8]([F:14])=[N:9][C:10]([Cl:26])=[CH:11][CH:12]=2)=[C:4]([CH:3]=1)[C:17]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:23]

参加物

5

反応物 2

HCID 24813Phosphorus oxychlorideHCID 667281373-(4-Bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide

生成物 1

HCID 86640732HCID 86640732、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-(4-bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide (420 mg, 1.096 mmol) in 15 mL of DCM was added dropwise phosphorus oxychloride (301 μL, 3.29 mmol) followed by 2 drops of DMF. After stirring at rt for 1 h, the reaction was quenched with sat. NaHCO3, extracted into EtOAc, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude was purified by column chromatography (DCM to DCM/EtOAc gradient beginning from 10:1 to 5:1 to 3:1) gave 5-bromo-2-(6-chloro-2-fluoropyridin-3-yloxy)-N,N-diethylbenzamide as a colorless gum.

後処理

  1. customthe reaction was quenched with sat. NaHCO3
  2. extractionextracted into EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by column chromatography (DCM to DCM/EtOAc gradient beginning from 10:1 to 5:1 to 3:1)

出典と根拠

ORDレコード
ord-a8232490459e4e408e54954e5f090fb4
出典データセット
uspto-grants-2016_05
特許番号
US09346827B2

反応ノート

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