Sodium hydride → isopropyl N-(4-pyridylmethyl)-2-bromo-4-methyl-5-imidazole carboxylate

HRID 280799

Reaction equation

[H-].[Na+].[Br:3][C:4]1[NH:5][C:6]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[C:7]([CH3:9])[N:8]=1.Cl[CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1>O1CCCC1>[N:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:5]2[C:6]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[C:7]([CH3:9])[N:8]=[C:4]2[Br:3])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 195 milligrams (mg) (8.13 mM) of sodium hydride in 20 ml of anhydrous tetrahydrofuran was added, in portions, 2 g (8.13 mM) of isopropyl 2-bromo-4-methyl-5-imidazolecarboxylate. The resulting suspension was cooled to 0° C. and 1.03 g (8.13 mM) of 4-chloromethylpyridine was added. The reaction mixture was stirred overnight at 50° C. The precipitated sodium chloride was removed by filtration and concentration in vacuo of the filtrate gave 2.5 g (92%) of isopropyl N-(4-pyridylmethyl)-2-bromo-4-methyl-5-imidazole carboxylate as a tan solid.

Workup

customThe precipitated sodium chloride was removed by filtration and concentration in vacuo of the filtrate

Sources & evidence

ORD record: ord-dbb495aba34848dc857773c0f1cfbd27
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04591377

Linked notes

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