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

HRID 1897513Notes

Reaction equation

HRID 1897513 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-7be280b835834f50aed5d9d884354cc8
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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