Bromotrimethylsilane → HCID 86697078, compound

HRID 626789Notes

Reaction equation

HRID 626789 reaction equation
Cl[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])[N:10]=[C:6]2[C:5]([F:20])=[CH:4][N:3]=1.[Br:21][Si](C)(C)C>C(#N)CC>[Br:21][C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])[N:10]=[C:6]2[C:5]([F:20])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86697079HCID 86697079, compound

Product 1

HCID 86697078HCID 86697078, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
80 °C

Procedure

2-(4-Chloro-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-3-fluorobenzonitrile (520 mg, 1.79 mmol) was suspended in propionitrile (35 mL), under an atmosphere of nitrogen and bromotrimethylsilane (0.646 mL, 6.76 mmol) was added. The reaction mixture was heated at 80° C. for 4.5 hours. The resultant mixture was cooled to room temperature 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 dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the title compound as a solid (600 mg, 100% yield). This was used in the next step without purification. LCMS (Method F): RT=3.30 min, m/z: 335 [M+H+].

Workup

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

Sources & evidence

ORD record
ord-a8c9a0c50e6c485b851a62505a8950ec
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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