Sodium Acetate → Ethyl pyrrolo[2,1-f][1,2,4]triazine-7-carboxylate

HRID 1773530Notes

Reaction equation

HRID 1773530 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:14]2[C:9]([C:10](Cl)=[N:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].C([O-])(=O)C.[Na+]>C(OCC)(=O)C.C(O)(C)C.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4]([C:6]1[N:14]2[C:9]([CH:10]=[N:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 58056298Ethyl 4-chloropyrrolo[2,1-f][1,2,4]triazine-7-carboxylate

Product 1

HCID 58056327Ethyl pyrrolo[2,1-f][1,2,4]triazine-7-carboxylateYield 44.3%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chloro-pyrrolo[2,1-f][1,2,4]triazine-7-carboxylic acid ethyl ester (120 mg), palladium hydroxide on carbon (20%, 40 mg) and sodium acetate (600 mg) in a mixture of ethyl acetate and isopropanol (5/1, 12 mL) was stirred at room temperature under hydrogen atmosphere (balloon pressure) overnight. The resulting mixture was filtered and a CELITE™ pad, the filtrate was evaporated under reduced pressure. The crude residue was purified by flash chromatography to give 45 mg of pyrrolo[2,1-f][1,2,4]triazine-7-carboxylic acid ethyl ester.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customa CELITE™ pad, the filtrate was evaporated under reduced pressure
  3. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-54a64bf4f47a47258cc3873114b64f68
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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