Imidazole → Ethyl4-(4-imidazol-1-yl-methyl-3-methyl-phenylethynyl)-benzoate

HRID 381138Notes

Reaction equation

HRID 381138 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH2:8]([O:10][C:11](=[O:29])[C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][C:23](CBr)=[C:22]([CH3:28])[CH:21]=2)=[CH:14][CH:13]=1)[CH3:9].[CH2:30](OC(=O)C1C=CC(CC(C)C2C=CC(CBr)=CC=2)=CC=1)C>CN(C=O)C>[CH2:8]([O:10][C:11](=[O:29])[C:12]1[CH:13]=[CH:14][C:15]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][C:23]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[C:22]([CH3:28])[C:21]=2[CH3:30])=[CH:16][CH:17]=1)[CH3:9]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 22568891Ethyl4-(4-bromomethyl-3-methyl-phenylethynyl)-benzoateHCID 86757501Ethyl4-(4-bromomethyl-methyl-phenylethyl)-benzoate

Product 1

HCID 69549307Ethyl4-(4-imidazol-1-yl-methyl-3-methyl-phenylethynyl)-benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of imidazole (30.0 mg, 0.44 mmol) in 2 mL DMF was treated with NaH (11.0 mg, 0.44 mmol) and heated to 90° C. After 1 h a solution of ethyl4-(4-bromomethyl-3-methyl-phenylethynyl)-benzoate (Intermediate 137, 120.0 mg, 0.34 mmol) in 2 mL DMF was added and stirring at 90° C. continued for 1 hour. The solution was cooled to room temperature and concentrated under reduced pressure. The title compound, 90.0 mg (71%) was isolated by column chromatography (20-100% EtOAc-hexanes) as a colorless solid.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ec2371f25c734624a1c4e2d6602820fc
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

Loading…