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

HRID 2117129Notes

Reaction equation

HRID 2117129 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.C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:19][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

4

Reactant 2

HCID 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 AKIN (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-bbbe905d422f4b62bebbfbf6a0bb124f
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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