Acetic Acid → Ethyl 3-bromo-6-cyano-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 518127Notes

Reaction equation

HRID 518127 reaction equation
[C:1]([C:3]1[C:4]2[S:15][C:14]([CH3:16])=[CH:13][C:5]=2[NH:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:2].[Br:17]N1C(=O)CCC1=O.C(O)(=O)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:17][C:13]1[C:5]2[NH:6][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:3]([C:1]#[N:2])[C:4]=2[S:15][C:14]=1[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 90254528Ethyl 6-cyano-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

Product 1

HCID 90254475Ethyl 3-bromo-6-cyano-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylateYield 49.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl 6-cyano-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate (0.3 g), N-Bromosuccinimide (0.24 g) and acetic acid (2.5 mL) were dissolved in chloroform (5.0 mL) and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and concentrated under reduced pressure. The obtained residue was washed with diethyl ether, and dried under reduced pressure to give the title compound (0.20 g).

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated under reduced pressure
  3. washThe obtained residue was washed with diethyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-c935402b187e497290f743747f7c3933
Source dataset
uspto-grants-2015_08
Patent number
US09115144B2

Reaction notes

Loading…