Methyl Thioglycolate → Methyl 3-amino-4-chlorothieno[3,2-c]pyridine-2-carboxylate

HRID 442777Notes

Reaction equation

HRID 442777 reaction equation
[C:1]([C:3]1[C:4]([Cl:10])=[N:5][CH:6]=[CH:7][C:8]=1Cl)#[N:2].[C:11]([O:15][CH3:16])(=[O:14])[CH2:12][SH:13].CC([O-])(C)C.[K+].C1COCC1>CN(C=O)C>[NH2:2][C:1]1[C:3]2[C:4]([Cl:10])=[N:5][CH:6]=[CH:7][C:8]=2[S:13][C:12]=1[C:11]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 219978282,4-Dichloropyridine-3-carbonitrileHCID 66863523KOtBu THF

Product 1

HCID 18796968Methyl 3-amino-4-chlorothieno[3,2-c]pyridine-2-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-cyano-2,4dichloropyridine (653 mg) and methyl thioglycolate (340 μL) in DMF (12 mL) at 5° C. was added a solution of 1.0M KOtBu/THF (4.5 mL). The reaction was stirred 20 min at 5° then 1 h at RT, then quenched in sat'd NH4Cl, the solid precipitate collected, washed with water and sucked dry to give 800 mg (88%) of the title compound.

Workup

  1. custom1 h at RT, then quenched in sat'd NH4Cl
  2. customthe solid precipitate collected
  3. washwashed with water
  4. customsucked dry

Sources & evidence

ORD record
ord-e0198dc6d6a149249ce80b29e6c9a33c
Source dataset
uspto-grants-1999_04
Patent number
US05891882

Reaction notes

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