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

HRID 1935937Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].BrC[C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][C:18]2[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=2)=[CH:12][C:11]=1[CH3:29].[CH3:30]N(C=O)C>>[N:1]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[C:17][C:18]3[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][CH:28]=3)=[C:12]([CH3:30])[C:11]=2[CH3:29])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Reactant 4

HCID 795Imidazole

HCID 6228Dimethylformamide2×

HCID 24758Sodium hydride

HCID 22568891Ethyl4-(4-bromomethyl-3-methyl-phenylethynyl)-benzoate2×

Product 1

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

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 ethyl 4-(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

temperatureThe solution was cooled to room temperature
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-81022be60a9449ffb36a9ec98040cdcf
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06387892B1

Reaction notes

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