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

HRID 1053155Notes

Reaction equation

HRID 1053155 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f1ecf1195e48462189d9e1c445ffe586
Source dataset
uspto-grants-2016_07
Patent number
US09393235B2

Reaction notes

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