Benzoyl Peroxide → 2-(bromomethyl)-4-(1H-pyrazol-1-yl)pyridine

HRID 41596Notes

Reaction equation

HRID 41596 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:5]=[CH:4][N:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 672531852-methyl-4-(1H-pyrazol-1-yl)pyridine

Product 1

HCID 683332632-(bromomethyl)-4-(1H-pyrazol-1-yl)pyridineYield 45%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 2-methyl-4-(1H-pyrazol-1-yl)pyridine (300 mg, 1.9 mmol) in CCl4 (25 mL), N-bromo succinimide (304 mg, 1.71 mmol) and benzoyl peroxide (23 mg, 0.09 mmol) were added and heated to reflux for 16 h. The reaction mixture was cooled to rt and precipitated succinimide was filtered. The filtrate was absorbed on silicagel and concentrated under reduced pressure. The crude product was purified flash column chromatography (eluent: 5% ethyl acetate in hexane) to yield the title compound (100 mg, 45%). [TLC Rf=0.34 (ethyl acetate/hexane 30:70)].

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. customprecipitated succinimide
  4. filtrationwas filtered
  5. customThe filtrate was absorbed on silicagel and
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified flash column chromatography (eluent: 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-736c82ea19d641148ef33681d341c8c0
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

Loading…