Trimethylsilyl iodide → 5-Fluoro-2-[1-(2-oxoethyl)-1H-indazol-5-yloxy]-benzonitrile

HRID 2112218Notes

Reaction equation

HRID 2112218 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:16]=3[C:17]#[N:18])=[CH:11][CH:12]=2)[CH:7]=[N:6]1.I[Si](C)(C)C.C([O-])(O)=O.[Na+]>ClCCl>[F:23][C:20]1[CH:21]=[CH:22][C:15]([O:14][C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[N:5]([CH2:4][CH:3]=[O:2])[N:6]=[CH:7]3)=[C:16]([CH:19]=1)[C:17]#[N:18]

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 666711532-(1-(2,2-dimethoxyethyl)-1H-indazol-5-yloxy)-5-fluorobenzonitrile

Product 1

HCID 574187725-Fluoro-2-[1-(2-oxoethyl)-1H-indazol-5-yloxy]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[1-(2,2-dimethoxyethyl)-1H-indazol-5-yloxy]-5-fluorobenzonitrile (1.42 g, 4.16 mmol) in dichloromethane (62 mL) was added iodotrimethylsilane (3.33 g, 16.64 mmol) portion-wise over 3 hours. The mixture was stirred at room temperature for 2 hours. Aqueous NaHCO3 (60 mL) was added to the mixture and it was extracted with ethyl acetate (2×50 mL). The combined extracts were washed with Na2S204, brine, dried over MgSO4, and concentrated under reduced pressure. The crude product was used in the next reaction without further purification.

Workup

  1. extractionwas extracted with ethyl acetate (2×50 mL)
  2. washThe combined extracts were washed with Na2S204, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was used in the next reaction without further purification

Sources & evidence

ORD record
ord-714b76c54be94ec288a76e05f2b2d4fd
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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