Trimethylsilyl iodide → HCID 86728490, compound

HRID 1053185Notes

Reaction equation

HRID 1053185 reaction equation
[C:1]([C:5]1[CH:21]=[CH:20][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([O:18]C)[CH:13]=2)=[O:10])=[C:7]([O:22][C:23]2[CH:24]=[N:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Si](I)(C)(C)C>C(#N)C>[C:1]([C:5]1[CH:21]=[CH:20][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[CH:13]=2)=[O:10])=[C:7]([O:22][C:23]2[CH:24]=[N:25][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:27][CH:28]=2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86728489HCID 86728489, compound

Product 1

HCID 86728490HCID 86728490, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To the 4-(tert-butyl)-N-(2-methoxypyridin-4-yl)-2-((6-(trifluoromethyl)pyridin-3-yl)oxy)benzamide (137 mg, 0.3 mmol) in acetonitrile (4.9 mL) was added TMSI (93.3 μL, 0.66 mmol). The reaction was stirred at 50° C. for 12 hours. The reactions was cooled to 25° C., filtered and purified by reverse phase HPLC (10-99% ACN in Water with HCl as a modifier) to yield 4-(tert-butyl)-N-(2-oxo-1,2-dihydropyridin-4-yl)-2-((6-(trifluoromethyl)pyridin-3-yl)oxy)benzamide (141) (14.4 mg, 13%). ESI-MS m/z calc. 431.15. found 432.3 (M+1)+; Retention time: 1.78 minutes (3 minutes run).

Workup

  1. temperatureThe reactions was cooled to 25° C.
  2. filtrationfiltered
  3. custompurified by reverse phase HPLC (10-99% ACN in Water with HCl as a modifier)

Sources & evidence

ORD record
ord-df16ec56fbbc4a5e90a3fc8d0cb5a42f
Source dataset
uspto-grants-2016_07
Patent number
US09393235B2

Reaction notes

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