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

HRID 1715653Notes

Reaction equation

HRID 1715653 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 Na2S2O4, 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 Na2S2O4, 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-4b517bbaa7f942e8bc860697c29b677f
Source dataset
uspto-grants-2010_09
Patent number
US07799782B2

Reaction notes

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