Bromotrimethylsilane → HCID 86697076, compound

HRID 626784Notes

Reaction equation

HRID 626784 reaction equation
[Cl:1][C:2]1[C:3]([N:11]2[CH:21]=[C:14]3[C:15](Cl)=[N:16][CH:17]=[C:18]([F:19])[C:13]3=[N:12]2)=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].[Br:22][Si](C)(C)C>C(#N)CC>[Br:22][C:15]1[C:14]2=[CH:21][N:11]([C:3]3[C:2]([Cl:1])=[CH:9][C:8]([F:10])=[CH:7][C:4]=3[C:5]#[N:6])[N:12]=[C:13]2[C:18]([F:19])=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86697075HCID 86697075, compound

Product 1

HCID 86697076HCID 86697076, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
80 °C

Procedure

3-Chloro-2-(4-chloro-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-5-fluorobenzonitrile (735 mg, 2.26 mmol) was suspended in propionitrile (44 mL), under an atmosphere of nitrogen and bromotrimethylsilane (0.82 mL, 5.64 mmol) was added. The reaction mixture was heated at 80° C. for 5 hours. The resultant mixture was cooled to room temperature and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound as a beige solid (834 mg, 100% yield). 1H NMR (300 MHz, CDCl3): δ 8.38 (d, J=2.3 Hz, 1H), 8.03 (d, J=3.0 Hz, 1H), 7.65 (dd, J=7.6, 2.8 Hz, 1H), 7.56 (dd, J=7.0, 2.8 Hz, 1H).

Workup

  1. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45ddea5067f8400ea0eb79fdb31c3256
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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