2-Bromobenzyl bromide → 3-[3-(2-Bromobenzyl)-3H-imidazol-4-yl]propionic acid methyl ester

HRID 923273Notes

Reaction equation

HRID 923273 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1.[Br:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34]Br>CC#N.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[N:7]([CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=2[Br:31])[CH:8]=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 769652-Bromobenzyl bromideHCID 10475868Methyl 3-(1-Tritylimidazol-4-yl) Propionate

Product 1

HCID 588271303-[3-(2-Bromobenzyl)-3H-imidazol-4-yl]propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(1-trityl-1H-imidazol-4-yl)propanoic acid methyl ester (5.0 g, 12.6 mmol) in CH3CN (80 mL) is added a solution of 2-bromobenzylbromide (2.84 g, 11.4 mmol) in CH3CN (20 mL). The resulting clear solution is stirred at ambient temperature over the weekend. The mixture is concentrated and the remaining oil is taken up in 85 mL methanol and heated up at 70° C. for 2 h. Then the mixture is concentrated to give a yellow oil, which is taken up in EtOAc and washed with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, and concentrated to yield a viscous oil. The crude reaction mixture is subjected to flash chromatography (silica gel) eluting with MeOH:CH2Cl2 to give the desired compound. MS (ESI) m/z 323 (M+H).

Workup

  1. concentrationThe mixture is concentrated
  2. temperatureheated up at 70° C. for 2 h
  3. concentrationThen the mixture is concentrated
  4. customto give a yellow oil, which
  5. washwashed with saturated aqueous NaHCO3 and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customto yield a viscous oil
  9. customThe crude reaction mixture
  10. washeluting with MeOH

Sources & evidence

ORD record
ord-6f18e6415c5046658796b2ede4b467d3
Source dataset
uspto-grants-2016_03
Patent number
US09278969B2

Reaction notes

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