Acetonitrile → Methyl [4-(4-imidazol-1-yl-methyl-3-isopropyl-phenylethynyl)-phenyl]-acetate

HRID 395204Notes

Reaction equation

HRID 395204 reaction equation
BrCC1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=2)=[CH:5][C:4]=1C(C)C.[C:25]([N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1)(=O)[CH3:26].[C:33]([O-])([O-])=O.[Na+].[Na+].[CH3:39][C:40]#N>O>[N:28]1([C:25]2[CH:4]=[CH:5][C:6]([C:9]#[C:10][C:11]3[CH:12]=[CH:13][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:16]=3)=[C:7]([CH3:8])[C:26]=2[CH:40]([CH3:39])[CH3:33])[CH:32]=[CH:31][N:30]=[CH:29]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 86585936Methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate2×

Product 1

HCID 86585935Methyl [4-(4-imidazol-1-yl-methyl-3-isopropyl-phenylethynyl)-phenyl]-acetateYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate (Intermediate 156, 72.0 mg, 0.19 mmol) and 1-acetylimidazole (22.0 mg, 0.20 mmol) in 5 mL CH3CN was heated at 65° C. for 8 h and then at 55° C. for 16 hours. The solution was cooled to room temperature, diluted with H2O and made basic by addition of Na2CO3, and extracted with EtOAc. The combined organic layers were washed with H2O and saturated aqueous NaCl, dried (MgSO4), and concentrated under reduced pressure. Column chromatography (0.5% Et3N in 5% MeOH-EtOAc) afforded 40.0 mg (58%) of the title compound as a colorless solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with H2O and saturated aqueous NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d19e8a60b5d04cf18ff49ad98ac0f865
Source dataset
uspto-grants-2003_08
Patent number
US06603019B2

Reaction notes

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