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

HRID 518126Notes

Reaction equation

HRID 518126 reaction equation
Br[C:2]1[C:3]2[S:14][C:13]([CH3:15])=[CH:12][C:4]=2[NH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].O.[CH3:17][N:18]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:17]([C:2]1[C:3]2[S:14][C:13]([CH3:15])=[CH:12][C:4]=2[NH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:18]

Participants

6

Reactant 3

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 1448019ethyl 6-bromo-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

Product 1

HCID 90254528Ethyl 6-cyano-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
150 °C

Procedure

To a solution of ethyl 6-bromo-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate (0.96 g) in N-methylpyrrolidone (10 mL) were added zinc cyanide (1.17 g) and tetrakis(triphenylphosphine)palladium (0.38 g), and the mixture was stirred at 150° C. for 30 minutes using microwave reactor. To the reaction solution was added water and the resulting mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (0.64 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe obtained residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3181c9b3dfac403cb4bed4ff4c0ec3d1
Source dataset
uspto-grants-2015_08
Patent number
US09115144B2

Reaction notes

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