Ethanol → Ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate

HRID 1713064

Reaction equation

HRID 1713064 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[SH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[Na+].[Na+].CCO>O>[NH2:9][C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[S:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 12185Ethyl ThioglycolateHCID 810792-Chloronicotinonitrile

Product 1

HCID 738459Ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylateYield 93.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloro-3-cyanopyridine (330 g, 2.38 mol), ethyl 2-mercaptoacetate (361.2 g, 3.01 mol), sodium carbonate (265 g, 2.5 mol) and EtOH (1.2 l) was heated to reflux for 4.5 h. The reaction mixture was then cooled to ambient temperature and added to water (15 l). The resulting slurry was stirred for 0.5 h then filtered. The filter cake was washed with two portions of water (2×2.5 l). The solids were then dried to constant weight under vacuum at 45° C. to yield the title compound as a brown solid (493 g, 93%). δH (CDCl3) 8.68 (1H, dd, J 4.7, 1.2 Hz), 7.93 (1H, dd, J 8.5, 1.2 Hz), 7.29 (1H, dd, J 8.5, 4.7 Hz), 5.90 (2H, br), 4.38 (2H, q, J 7.0 Hz), 1.40 (3H, t, J 7.0 Hz). LCMS RT 2.9 minutes, 223 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 h
  3. filtrationthen filtered
  4. washThe filter cake was washed with two portions of water (2×2.5 l)
  5. customThe solids were then dried to constant weight under vacuum at 45° C.

Sources & evidence

ORD record
ord-754035339ba0479390b91ed3f2896832
Source dataset
uspto-grants-2010_09
Patent number
US07795256B2

Linked notes

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