Bromotrimethylsilane → 4-(4-Bromo-7-chloropyrazolo[4,3-c]pyridin-2-yl)-3,5-dichlorobenzonitrile

HRID 626746Notes

Reaction equation

HRID 626746 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:21])[C:9]=1[N:10]1[CH:20]=[C:13]2[C:14](Cl)=[N:15][CH:16]=[C:17]([Cl:18])[C:12]2=[N:11]1)[C:5]#[N:6].[Br:22][Si](C)(C)C>C(#N)CC>[Br:22][C:14]1[C:13]2=[CH:20][N:10]([C:9]3[C:2]([Cl:1])=[CH:3][C:4]([C:5]#[N:6])=[CH:7][C:8]=3[Cl:21])[N:11]=[C:12]2[C:17]([Cl:18])=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 866970503,5-Dichloro-4-(4,7-dichloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile

Product 1

HCID 866970624-(4-Bromo-7-chloropyrazolo[4,3-c]pyridin-2-yl)-3,5-dichlorobenzonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Procedure

A mixture of 3,5-dichloro-4-(4,7-dichloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile (250 mg, 0.70 mmol) and bromotrimethylsilane (0.462 mL, 3.50 mmol) in propionitrile (4.0 mL) was heated under reflux for 4 hours. The resultant mixture was cooled and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The layers were separated and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound as a beige solid (273 mg, 97% yield). 1H NMR (400 MHz, CDCl3): δ 8.30 (s, 1H), 8.16 (s, 1H), 7.85 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  5. customThe layers were separated
  6. washthe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-678ac4b616424ec9b21abb5b00de25db
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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