1,8-Diazabicyclo(5.4.0)undec-7-ene → Phenylmethyl 3-(2,4-dichlorophenyl)pyrrole-2-carboxylate

HRID 2242027Notes

Reaction equation

HRID 2242027 reaction equation
C1CCN2C(=NCCC2)CC1.[Cl:12][C:13]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:14]=1[CH:15]=[CH:16][N+]([O-])=O.[N+:25]([CH2:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])#[C-:26]>C1COCC1>[Cl:12][C:13]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:14]=1[C:15]1[CH:16]=[CH:26][NH:25][C:27]=1[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2558822,4-DichloronitrostyreneHCID 561774Benzyl 2-isocyanoacetate

Product 1

HCID 58914796Phenylmethyl 3-(2,4-dichlorophenyl)pyrrole-2-carboxylateYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DBU (1 eq) was added to a stirred solution of 2,4-Dichloronitrostyrene (1) (1 eq) and benzyl 2-isocyanoacetate (0.9 eq) in THF at −78° C. under N2. The reaction was allowed to warm to room temperature over 2 h. The reaction could be followed by TLC eluting with CHCl3 (Rf0.3). After stirring for an additional 12 h, the reaction was diluted with CH2Cl2 and EtOAc. The organic mixture washed with 0.1 N HCl, water, sat. aq. NaHCO3, brine, dried (Na2SO4), filtered and concentrated under reduced pressure to an oil. The crude product was purified using silica column chromatography eluting with CHCl3 to obtain pure phenylmethyl 3-(2,4-dichlorophenyl)pyrrole-2-carboxylate (2) (15% yield).

Workup

  1. customThe reaction
  2. washeluting with CHCl3 (Rf0.3)
  3. additionthe reaction was diluted with CH2Cl2 and EtOAc
  4. washThe organic mixture washed with 0.1 N HCl, water, sat. aq. NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to an oil
  8. customThe crude product was purified
  9. washeluting with CHCl3

Sources & evidence

ORD record
ord-2f6319e5539f487cafbbecbac776d573
Source dataset
uspto-grants-2010_03
Patent number
US07671049B2

Reaction notes

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