3-Aminopyridine → 5-Bromo-6-methoxy-N-(3-pyridyl)benzo-[b]thiophene-3-carboxamide

HRID 581993Notes

Reaction equation

HRID 581993 reaction equation
[Br:1][C:2]1[C:13]([O:14][CH3:15])=[CH:12][C:5]2[S:6][CH:7]=[C:8]([C:9]([OH:11])=O)[C:4]=2[CH:3]=1.[NH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1>S(Cl)(Cl)=O>[Br:1][C:2]1[C:13]([O:14][CH3:15])=[CH:12][C:5]2[S:6][CH:7]=[C:8]([C:9]([NH:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[O:11])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 537810295-Bromo-6-methoxybenzo[b]thiophene-3-carboxylic acid

Product 1

HCID 442131775-Bromo-6-methoxy-N-(3-pyridyl)benzo-[b]thiophene-3-carboxamideYield 23.3%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

5-Bromo-6-methoxybenzo[b]thiophene-3-carboxylic acid (D5) (0.36 g, 0.0013 mole) and thionyl chloride (20 ml) were heated under reflux for 1 hour, after which the reaction mixture was cooled to ambient temperature and evaporated in vacuo. The resulting acid chloride was dissolved in dry dichloromethane (30 ml) and acetonitrile (10 ml) under argon. 3-Aminopyridine (0.12 g, 0.0013 mole) was added and the reaction mixture stirred at ambient temperature for 16 hours. The solvent was removed in vacuo and the resulting solid basified with 10% sodium hydroxide solution, extracted into dichloromethane, dried (Na2SO4) and evaporated in vacuo. The resulting solid was recrystallised from ethyl acetate/methanol to afford the title compound (0.11 g, 23%) as a beige solid.

Workup

  1. temperatureunder reflux for 1 hour
  2. customevaporated in vacuo
  3. dissolutionThe resulting acid chloride was dissolved in dry dichloromethane (30 ml)
  4. customThe solvent was removed in vacuo
  5. extractionextracted into dichloromethane
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe resulting solid was recrystallised from ethyl acetate/methanol

Sources & evidence

ORD record
ord-da20ae4ccbd441ddb1db182aa7887a98
Source dataset
uspto-grants-1999_07
Patent number
US05922733

Reaction notes

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