Phosphorus oxychloride → Ethyl 4-chloropyrrolo[2,1-f][1,2,4]triazine-7-carboxylate

HRID 1773529Notes

Reaction equation

HRID 1773529 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:14]2[C:9]([C:10](=O)[NH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:18])=O>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:14]2[C:9]([C:10]([Cl:18])=[N:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136385527HCID 136385527, compound

Product 1

HCID 58056298Ethyl 4-chloropyrrolo[2,1-f][1,2,4]triazine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-7-carboxylic acid ethyl ester (300 mg) and phosphorus oxychloride (1 mL) was heated at 160° C. for 15 minutes in a microwave reactor. The resulting mixture was cooled and poured into a mixture of ice-water and ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (hexane/EtOAc, 90/10) to afford 120 mg of 4-chloro-pyrrolo[2,1-f][1,2,4]triazine-7-carboxylic acid ethyl ester containing 4-chloro-pyrrolo[2,1-f][1,2,4]triazine-7-carbonitrile.

Workup

  1. temperatureThe resulting mixture was cooled
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography (hexane/EtOAc, 90/10)

Sources & evidence

ORD record
ord-0a93bd731c4e48ab91396d7a4d8ca989
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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