Methyl 3-aminothieno(2,3-b)pyridine-2-carboxylate → Methyl thieno[2,3-b]pyridine-2-carboxylate

HRID 15423

Reaction equation

HRID 15423 reaction equation
N[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].N([O-])=O.[Na+]>>[S:4]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[CH:2]=[C:3]1[C:11]([O:13][CH3:14])=[O:12]

Participants

3

Reactant 2

HCID 2820896Methyl 3-aminothieno(2,3-b)pyridine-2-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 19007380Methyl thieno[2,3-b]pyridine-2-carboxylate

Procedure

The synthesis is carried out according to the general procedure; for work-up, the resulting precipitate is filtered off with suction and washed twice with water and three times with ethyl acetate. The organic phase of the resulting filtrate is separated off, dried and concentrated. Using 0.22 g (1.07 mmol) of methyl 3-aminothieno[2,3-b]pyridine-2-carboxylate and 0.24 g (3.41 mmol) of sodium nitrite, 84 mg (41% of theory) of the desired product are obtained.

Workup

  1. filtrationfor work-up, the resulting precipitate is filtered off with suction
  2. washwashed twice with water and three times with ethyl acetate
  3. customThe organic phase of the resulting filtrate is separated off
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-92077d7b20d8411693216d3d67a73140
Source dataset
uspto-grants-2010_06
Patent number
US07732477B2

Linked notes

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