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

HRID 909231Notes

Reaction equation

HRID 909231 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-5a4d147762ed41dbab69008ce4611efe
Source dataset
uspto-grants-2011_09
Patent number
US08017641B2

Reaction notes

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