Potassium Carbonate → Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate

HRID 876761Notes

Reaction equation

HRID 876761 reaction equation
Cl[C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[C:16]([O:20][CH3:21])(=[O:19])[CH2:17][SH:18]>CN(C=O)C.O>[NH2:9][C:8]1[C:3]2=[N:4][CH:5]=[CH:6][CH:7]=[C:2]2[S:18][C:17]=1[C:16]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 8182583-Chloropyridine-2-carbonitrile

Product 1

HCID 13793447Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 3-chloropyridine-2-carbonitrile (C-1) (1.01 g, 7.29 mmol) and K2CO3 (1.10 g, 7.96 mmol) in DMF (10 mL) and water (1 mL) was added methyl thioglycolate (0.709 mL, 7.93 mmol) dropwise. The reaction mixture was stirred at 40° C. for 3 h. The mixture was quenched with cold water (70 mL) and placed on ice to enhance precipitation. The precipitate was collected by filtration to afford the title compound. MS (m/z): 209 (M+1)+.

Workup

  1. customThe mixture was quenched with cold water (70 mL)
  2. customprecipitation
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-7675fb16b1c14fed91e156a653fbbb99
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

Loading…