Diethyl Ether → HCID 59251284, compound

HRID 1466419Notes

Reaction equation

HRID 1466419 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 NH4Cl, 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 NH4Cl
  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-9fa3702bd34e47098ef96a458ce97bc7
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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