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

HRID 658153Notes

Reaction equation

HRID 658153 reaction equation
N[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].N([O-])=O.[Na+]>>[S:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[CH:2]=[C:3]1[C:11]([O:13][CH3:14])=[O:12]

Participants

3

Reactant 2

HCID 13793447Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 22047416Methyl thieno(3,2-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 repeatedly with water, ethyl acetate and THF. The organic phases of the resulting filtrates are separated off, the aqueous phase is washed with ethyl acetate and the combined organic phases are dried and concentrated. The resulting product is purified by preparative HPLC. Using 2.40 g (11.53 mmol) of methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate and 2.54 g (36.88 mmol) of sodium nitrite, 0.12 g (5% of theory) of the desired product are obtained.

Workup

  1. filtrationfor work-up, the resulting precipitate is filtered off with suction
  2. washwashed repeatedly with water, ethyl acetate and THF
  3. customThe organic phases of the resulting filtrates are separated off
  4. washthe aqueous phase is washed with ethyl acetate
  5. customthe combined organic phases are dried
  6. concentrationconcentrated
  7. customThe resulting product is purified by preparative HPLC

Sources & evidence

ORD record
ord-6a0cc1f90e2548659bf8931fdf6e1dc2
Source dataset
uspto-grants-2011_12
Patent number
US08076355B2

Reaction notes

Loading…