4-(3-Methyl-3H-imidazole-4-carbonyl)-2-(naphthalen-2-yloxy)-benzonitrile → 4-[1-hydroxy-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2-(naphthalen-2-yloxy)-benzonitrile

HRID 379066Notes

Reaction equation

HRID 379066 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([O:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=3)[CH:10]=2)=[O:8])=[CH:5][N:4]=[CH:3]1.[CH3:28][Mg+].[Br-]>C1COCC1>[OH:8][C:7]([C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([O:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[CH:10]=1)([C:6]1[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=1)[CH3:28]

Participants

4

Reactant 2

HCID 216969884-(3-Methyl-3H-imidazole-4-carbonyl)-2-(naphthalen-2-yloxy)-benzonitrileHCID 178418689HCID 178418689, compound

Product 1

HCID 98206624-[1-hydroxy-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2-(naphthalen-2-yloxy)-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(3-Methyl-3H-imidazole-4-carbonyl)-2-(naphthalen-2-yloxy)-benzonitrile (0.109 g, 0.308 mmol) was dissolved in anhydrous THF (5 mL) and a 3.0 M solution of MeMgBr (0.35 mL, 1.05 mmol) was added and stirred at RT. The reaction was quenched with NH4Cl after 1 h, concentrated, diluted with EtOAc, washed with satd. NaHCO3 solution, water, brine, dried (MgSO4) and concentrated to give the title compound. FT/ICR MS (M+1)=370.

Workup

  1. customThe reaction was quenched with NH4Cl after 1 h
  2. concentrationconcentrated
  3. additiondiluted with EtOAc
  4. washwashed with satd
  5. dry with materialNaHCO3 solution, water, brine, dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-09380b77cf94411894cd35af679748d1
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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