Trimethylsilyl iodide → 5-chloro-2-fluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide

HRID 1053155ノート

反応式

HRID 1053155 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([CH:18]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([O:16]C)[CH:11]=1)=[O:8].[Si](I)(C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([CH:18]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][NH:13][C:12](=[O:16])[CH:11]=1)=[O:8]

参加物

4

反応物 2

HCID 85247Trimethylsilyl iodideHCID 867284685-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide

生成物 1

HCID 867284695-chloro-2-fluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide収率 26.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

To 5-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide (3.8 g, 13.50 mmol) in acetonitrile (126.3 mL) was added TMSI (7.7 mL, 54.00 mmol). The reaction was stirred at 50° C. overnight. The acetonitrile was evaporated and the crude re-dissolved in ethyl acetate. The organics were washed with water, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography using a gradient of ethyl acetate in hexanes (0-100%) and then methanol in dichloromethane (0-20%) yielded 5-chloro-2-fluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide (950 mg, 26%) as a white solid. ESI-MS m/z calc. 266.03. found 267.1 (M+1)+; Retention time: 1.24 minutes (3 minutes run).

後処理

  1. customThe acetonitrile was evaporated
  2. dissolutionthe crude re-dissolved in ethyl acetate
  3. washThe organics were washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-f1ecf1195e48462189d9e1c445ffe586
出典データセット
uspto-grants-2016_07
特許番号
US09393235B2

反応ノート

読み込み中…