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Trifluoroacetic acid → 5-Fluoro-6-methoxypyridin-3-amine

HRID 2171232
Notes
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Reaction equation

HRID 2171232 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([NH:17]C(=O)OC(C)(C)C)[CH:12]=[N:13][C:14]=1[O:15][CH3:16]>>[F:8][C:9]1[CH:10]=[C:11]([NH2:17])[CH:12]=[N:13][C:14]=1[O:15][CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89546885Tert-butyl (5-fluoro-6-methoxypyridin-3-yl)carbamate

Product 1

HCID 454803515-Fluoro-6-methoxypyridin-3-amineYield 11.6%

Procedure

TFA (2 ml) was added to tert-butyl (5-fluoro-6-methoxypyridin-3-yl)carbamate (279 mg) obtained in the 1st step, followed by stirring at room temperature for 1 hour. The solvent was distilled away under reduced pressure and a 5M sodium hydroxide aqueous solution was added to the obtained residue at 0° C. so as to alkalify the mixture, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate and the solvent was distilled away under reduced pressure. A light brown solid of 5-fluoro-6-methoxypyridin-3-amine (19 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  • distillationThe solvent was distilled away under reduced pressure
  • additiona 5M sodium hydroxide aqueous solution was added to the obtained residue at 0° C. so as
  • extractionfollowed by extraction with ethyl acetate
  • washThe organic layers were washed with saturated saline
  • dry with materialdried over anhydrous sodium sulfate
  • distillationthe solvent was distilled away under reduced pressure
  • Sources & evidence

    ORD record
    ord-13ba9d3b2d9846ecbc3e2d54e22544f8
    Source dataset
    uspto-grants-2015_06
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US09051310B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes