Formamide → 6-Bromopyrrolo[2,1-f][1,2,4]triazin-4-ol

HRID 1498835Notes

Reaction equation

HRID 1498835 reaction equation
C[O:2][C:3]([C:5]1[N:6]([NH2:11])[CH:7]=[C:8]([Br:10])[CH:9]=1)=O.[CH:12]([NH2:14])=O>C(OCC)(=O)C>[Br:10][C:8]1[CH:9]=[C:5]2[N:6]([CH:7]=1)[N:11]=[CH:12][NH:14][C:3]2=[O:2]

Participants

4

Reactant 2

HCID 713FormamideHCID 58423493Methyl 1-amino-4-bromo-1H-pyrrole-2-carboxylate

Product 1

HCID 1357420626-Bromopyrrolo[2,1-f][1,2,4]triazin-4-olYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-amino-4-bromo-1H-pyrrole-2-carboxylic acid methyl ester (2.9 g, 13.2 mmol) in formamide (12 mL) was heated at 180° C. for 5 hrs. The mixture was diluted with ethyl acetate (300 mL), and then washed with water (100 mL*2), brine (100 mL*3). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting solid was washed with PE/EA (4:1, 50 mL) to give 6-bromo-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (1.4 g, yield 50%) as yellow solid. MS (ES+) requires: 213, 215. found 214, 216 [M+H]+; purity: 92%.

Workup

  1. washwashed with water (100 mL*2), brine (100 mL*3)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting solid was washed with PE/EA (4:1, 50 mL)

Sources & evidence

ORD record
ord-a203289500ba4e13b16ed669d2fe079c
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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