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

HRID 658152

Reaction equation

HRID 658152 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-28e46e2cb2014e02ab6e4d0a5b122ce3
Source dataset
uspto-grants-2011_12
Patent number
US08076355B2

Linked notes

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