HCID 86608217, compound → HCID 11842687, compound

HRID 1782101Notes

Reaction equation

HRID 1782101 reaction equation
[N:1]([C:4](=[CH:10][C:11]1[N:12]([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)[CH:13]=[N:14][CH:15]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>CC1C=CC(C)=CC=1>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([N:12]2[C:11]3[CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH:1][C:15]=3[N:14]=[CH:13]2)=[CH:17][CH:18]=1

Participants

3

Reactant 1

HCID 86608217HCID 86608217, compound

Product 1

HCID 11842687HCID 11842687, compound

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A suspension of ethyl 2-azido-3-[3-(4-bromophenyl)-3H-imidazol-4-yl]acrylate (7) (240 mg) in p-xylene (10 mL) was heated at reflux under nitrogen for 30 min. The mixture was then cooled to rt, and the resulting white solid was collected by filtration, washed with hexane, and dried in air to yield ethyl 1-(4-bromophenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate EXAMPLE 1. LC-MS (ES+): m/z 334/336 (1/1) [MH+]. 1H NMR (CDCl3, 400 MHz): δ=1.40 (t, J=7.1 Hz, 3H), 4.38 (q, J=7.1 Hz, 2H), 6.94 (d, J=1.6 Hz, 1H), 7.43 (d, J=8.8 Hz, 2H), 7.65 (d, J=8.8 Hz, 2H), 7.93 (s, 1H), 8.99 (br s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 30 min
  3. filtrationthe resulting white solid was collected by filtration
  4. washwashed with hexane
  5. customdried in air

Sources & evidence

ORD record
ord-ace680e17e364703b31d189b7e87f60f
Source dataset
uspto-grants-2009_03
Patent number
US07498354B2

Reaction notes

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