Ethyl diazoacetate → HCID 67509258, compound

HRID 1400028Notes

Reaction equation

HRID 1400028 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:14])[NH:10][C:11](=[O:13])[CH:12]=2)=[CH:4][CH:3]=1.[CH2:15]([O:17][C:18](=[O:22])[CH:19]=[N+]=[N-])[CH3:16]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[CH:19]([C:18]([O:17][CH2:15][CH3:16])=[O:22])[CH:12]2[C:11](=[O:13])[NH:10][C:9]3=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 198434683-(4-Bromo-phenyl)-pyrrole-2,5-dione

Product 1

HCID 67509258HCID 67509258, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-(4-bromophenyl)-1H-pyrrole-2,5-dione (3.45 g, 13.74 mmol) obtained in Step 1 of Intermediate IX, in toluene (50 mL) was added ethyldiazoacetate (4.27 mL, 41.23 mmol). The reaction mixture was heated to reflux for 18 h. After completion of the reaction as confirmed by TLC, solvent was removed in vacuo to afford crude product which was purified by column chromatography (silica gel, 4:6 EtOAc:Pet. ether) to afford the title compound as a yellow solid (2.66 g, 57%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. customAfter completion of the reaction
  4. customwas removed in vacuo
  5. customto afford crude product which
  6. customwas purified by column chromatography (silica gel, 4:6 EtOAc:Pet. ether)

Sources & evidence

ORD record
ord-e36c8614fbff4d0bb91a29d464ca4901
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

Loading…