methyl 5-[(E)-2-(4-chlorophenyl)vinyl]4-nitrothiophene-2-carboxylate → methyl 5-(4-chlorophenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 505793Notes

Reaction equation

HRID 505793 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[S:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][C:11]=2[N+:19]([O-])=O)=[CH:4][CH:3]=1>P(OCC)(OCC)OCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:19][C:11]3[CH:12]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[S:14][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68471094methyl 5-[(E)-2-(4-chlorophenyl)vinyl]4-nitrothiophene-2-carboxylate

Product 1

HCID 24976015methyl 5-(4-chlorophenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 16%

Reagents, catalysts & solvents 1

HCID 31215Triethyl phosphiteSolvent

Procedure

A solution (1 M) of methyl 5-[(E)-2-(4-chlorophenyl)vinyl]4-nitrothiophene-2-carboxylate in triethyl phosphite was heated to reflux for 20 h. After cooling down a part of the solvent was evaporated under high vacuum (2 mbar, water bath 60° C.) then the residue was purified by flash chromatography on silica gel (1:20 acetone/toluene). Fractions containing the title compound along with some phosphorous impurities were concentrated to give a residue that was triturated with AcOEt/petroleum ether (1:9) and filtered to afford the title compound (16%) as a solid.

Workup

  1. temperatureto reflux for 20 h
  2. temperatureAfter cooling down a part of the solvent
  3. customwas evaporated under high vacuum (2 mbar, water bath 60° C.)
  4. customthe residue was purified by flash chromatography on silica gel (1:20 acetone/toluene)
  5. additionFractions containing the title compound along with some phosphorous impurities
  6. concentrationwere concentrated
  7. customto give a residue that
  8. customwas triturated with AcOEt/petroleum ether (1:9)
  9. filtrationfiltered

Sources & evidence

ORD record
ord-f530060722d943388bf23e24d7beb9a6
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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