Ethyl Thioglycolate → Methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate

HRID 734214Notes

Reaction equation

HRID 734214 reaction equation
[SH:1][CH2:2][C:3](OCC)=[O:4].[H-].[Na+].[NH2:10][C:11]1[N:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][C:12]=1Br>CN(C=O)C.CCOC(C)=O>[O:4]=[C:3]1[CH2:2][S:1][C:12]2[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[N:16][C:11]=2[NH:10]1

Participants

6

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 10704661Methyl 6-amino-5-bromopicolinate

Product 1

HCID 21873660Methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 2-mercaptoacetate (1.47 mL) in DMF (48 mL) was ice-cooled and treated with sodium hydride (540 mg of a 60% dispersion in oil). After 1 h methyl 6-amino-5-bromopyridine-2-carboxylate (3 g) (T. R. Kelly and F. Lang, J. Org. Chem. 61, 1996, 4623-4633) was added and the mixture stirred for 16 h at room temperature. The solution was diluted with EtOAc (1 L), washed with water (3×300 mL), dried and evaporated to about 10 mL. The white solid was filtered off and washed with a little EtOAc to give the ester (0.95 g); LC/MS (APCI−) m/z 223 ([M−H]−, 100%).

Workup

  1. temperaturecooled
  2. addition61, 1996, 4623-4633) was added
  3. washwashed with water (3×300 mL)
  4. customdried
  5. customevaporated to about 10 mL
  6. filtrationThe white solid was filtered off
  7. washwashed with a little EtOAc

Sources & evidence

ORD record
ord-92c8a08a6f1d4035b232fd711fadb25d
Source dataset
uspto-grants-2009_09
Patent number
US07592334B2

Reaction notes

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