Benzoyl Peroxide → 2-(1-Bromoethyl)-3-(3,5-difluorophenyl)pyrazolo[1,5-a]pyridine

HRID 408803Notes

Reaction equation

HRID 408803 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([CH2:18][CH3:19])=[N:11][N:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=23)[CH:5]=[C:6]([F:8])[CH:7]=1.[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH:18]([C:10]1[C:9]([C:4]2[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=2)=[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=1)[CH3:19]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 583793343-(3,5-Difluorophenyl)-2-ethylpyrazolo[1,5-a]pyridine

Product 1

HCID 583793362-(1-Bromoethyl)-3-(3,5-difluorophenyl)pyrazolo[1,5-a]pyridineYield 103.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-(3,5-Difluorophenyl)-2-ethylpyrazolo[1,5-a]pyridine (0.48 g, 1.8 mmol), N-bromosuccinimide (0.55 g, 3.1 mmol) and benzoyl peroxide (50 mg, 0.2 mmol) were stirred in carbon tetrachloride (20 mL). The mixture was heated to reflux for 2 hours. After removal of the solvent in vacuo, the residue was dissolved in dichloromethane, washed with water, saturated aqueous sodium sulfite, aqueous sodium bicarbonate and brine. The extracts were dried over sodium sulfate, filtered and concentrated to give the desired compound (0.63 g, 100%). LCMS for C15H12BrF2N2 (M+H)+: m/z=336.8, 338.8. 1H NMR (300 MHz, DMSO-d6): δ 8.78 (m, 1H), 7.70 (m, 1H), 7.30 (m, 4H), 7.02 (m, 1H), 5.63 (m, 1H), 2.17 (m, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customAfter removal of the solvent in vacuo
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with water, saturated aqueous sodium sulfite, aqueous sodium bicarbonate and brine
  6. dry with materialThe extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-37e95cddc9184e33823698d9d71d1d27
Source dataset
uspto-grants-2014_06
Patent number
US08759359B2

Reaction notes

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