Azobisisobutyronitrile → 5-(Bromomethyl)-4-chloropyrrolo[2,1-f][1,2,4]triazine

HRID 347523Notes

Reaction equation

HRID 347523 reaction equation
[Cl:1][C:2]1[C:7]2=[C:8]([CH3:11])[CH:9]=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:31])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:31][CH2:11][C:8]1[CH:9]=[CH:10][N:6]2[C:7]=1[C:2]([Cl:1])=[N:3][CH:4]=[N:5]2

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 218742274-Chloro-5-methylpyrrolo(2,1-f)(1,2,4)triazine

Product 1

HCID 218743865-(Bromomethyl)-4-chloropyrrolo[2,1-f][1,2,4]triazineYield 92%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-5-methyl-pyrrolo[2,1-f][1,2,4]triazine (2.0 g, 11.93 mmol, WO 03/042172) and AIBN (195 mg, 1.19 mmol) in CCl4 (80 mL) under N2 was heated to 100° C. for 5 min, NBS (2.55 g, 14.3 mmol) was added. The reaction mixture was stirred for 10 min, then cooled to rt, filtered. The CCl4 layer was washed with dilute NaHCO3 aqueous solution, dried (MgSO4), filtered and concentrated to give the desired product (2.70 g, 92%).

Workup

  1. temperaturecooled to rt
  2. filtrationfiltered
  3. washThe CCl4 layer was washed with dilute NaHCO3 aqueous solution
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f6683d8730884417b890543c1cf3e495
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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