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Ethyl Acetate → 6-Amino-5-ethoxycarbonylmethylthio-3-fluoropyridine-2-carboxylic acid methyl ester

HRID 1437352
Notes
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Reaction equation

HRID 1437352 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[CH3:10][O:11][C:12]([C:14]1[C:19]([F:20])=[CH:18][C:17](Br)=[C:16]([NH2:22])[N:15]=1)=[O:13].CCOC(C)=O>CN(C=O)C>[CH3:10][O:11][C:12]([C:14]1[C:19]([F:20])=[CH:18][C:17]([S:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:16]([NH2:22])[N:15]=1)=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 21873678Methyl 6-amino-5-bromo-3-fluoropicolinate

Product 1

HCID 218736466-Amino-5-ethoxycarbonylmethylthio-3-fluoropyridine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A solution of ethyl mercaptoacetate (1.15 ml) in DMF (40 ml) was ice-cooled under argon, treated with sodium hydride (420 mg of a 60% dispersion in oil) and stirred until all was in solution (about 1 hour). The ester (a) (2.48 g) was added, the mixture allowed to warm to room temp. and stirred overnight. EtOAc (150 ml) was added, the solution washed with water (3×150 ml), dried and evaporated. Chromatography of the residue (40% EtOAc in hexane) gave an oil (1.7 g).

Workup

  1. temperaturecooled under argon
  2. customall was in solution (about 1 hour)
  3. temperatureto warm to room temp.
  4. stirringstirred overnight
  5. washthe solution washed with water (3×150 ml)
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-deb2d3875d5543afac8e25d6bf8c4e6d
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07622481B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes