Diethyl Ether → HCID 59251284, compound

HRID 1046641Notes

Reaction equation

HRID 1046641 reaction equation
[CH3:1][Mg+].[Br-].CC[O:6][CH2:7][CH3:8].C(OC([C:14]1[N:15]=[C:16]([C:27]2[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][CH:28]=2)[N:17]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[CH:18]=1)=O)C>C1COCC1>[Br:33][C:30]1[CH:29]=[CH:28][C:27]([C:16]2[N:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[CH:18]=[C:14]([C:7]([OH:6])([CH3:8])[CH3:1])[N:15]=2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 59251254HCID 59251254, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 59251284HCID 59251284, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 3.0 M solution of MeMgBr in Et2O (1.0 mL, 3.0 mmol) at 0° C. added slowly a solution of 2-(4-bromophenyl)-1-(2-chlorobenzyl)-1H-imidazole-4-carboxylic acid ethyl ester (235 mg, 0.56 mmol) in THF (3 mL, anhyd). After addition was completed the flask was removed from the ice-water bath and allowed to warm to ambient temperature. At 40 min the reaction mixture was quenched by addition of satd NH4 Cl, extracted with EtOAc, dried (MgSO4), concentrated and purified by chromatography (silica, EtOAc/Hex, 20:80 to 60:40) to give the title compound (135 mg, 59%) as a pale amber solid. 1H-NMR (DCM-d2): δ 7.54 (d, 2H), 7.38-7.45 (m, 3H), 7.24-7.33 (m, 2H), 6.89 (d, 1H), 6.82 (s, 1H), 5.25 (s, 2H), 2.86 (br s, 1H), 1.54 (s, 6H); MS (ES): 405, 407 [M+H]+.

Workup

  1. additionAfter addition
  2. customwas removed from the ice-water bath
  3. customAt 40 min the reaction mixture was quenched by addition of satd NH4 Cl
  4. extractionextracted with EtOAc
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by chromatography (silica, EtOAc/Hex, 20:80 to 60:40)

Sources & evidence

ORD record
ord-b83c43dde6f543c3913bda77315b5c10
Source dataset
uspto-grants-2013_10
Patent number
US08569352B2

Reaction notes

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