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

HRID 2358848

Reaction equation

HRID 2358848 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), ethyl 2-mercaptoacetate (361.2 g), sodium carbonate (265 g) and EtOH (1.2 L) was heated to reflux for 4.5 hours. It was then cooled to ambient temperature, added to water (10 L) and the addition was washed in with water (5 L). The resulting slurry was stirred for 30 minutes and then it was filtered. The filter cake was washed with two portions of water (2×2.5 L) and dried at the pump. The solids were then dried to constant weight under vacuum at 45° C. to yield the title compound as a brown solid (493.1 g, 93.2%). 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, b), 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 hours
  3. additionthe addition
  4. washwas washed in with water (5 L)
  5. filtrationit was filtered
  6. washThe filter cake was washed with two portions of water (2×2.5 L)
  7. customdried at the pump
  8. customThe solids were then dried to constant weight under vacuum at 45° C.

Sources & evidence

ORD record
ord-130e2f275342447983a1250fac652e5c
Source dataset
uspto-grants-2010_07
Patent number
US07763729B2

Linked notes

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