Benzyl Bromide → 1-benzyl-5-bromo-4-nitro-1h-imidazole

HRID 601299Notes

Reaction equation

[Br:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[N+:7]([O-:9])=[O:8].C(=O)(O)[O-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH2:15]([N:6]1[C:2]([Br:1])=[C:3]([N+:7]([O-:9])=[O:8])[N:4]=[CH:5]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of the product of Example 312A (2.3 g, 11.98 mmol) in anhydrous N,N-dimethylformamide (40 mL) at 25° C. was reacted with sodium bicarbonate (2.0 g, 24 mmol) and dropwise addition of benzyl bromide (1.58 mL, 13.17 mmol). The reaction was stirred for an additional 12 hours at 25° C. The reaction was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase column chromatography on a C18 column, eluting with a gradient of acetonitrile in water containing 0.1% trifluoroacetic acid (5:95 to 100) to give the title compound (1.63 g, 48%). MS (ESI+) m/z 284 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ ppm 5.38 (s, 2H), 7.24-7.42 (m, 5H), 8.28 (s, 1H).

Workup

concentrationThe reaction was concentrated under reduced pressure
customthe residue was partitioned between ethyl acetate and water
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by reverse phase column chromatography on a C18 column
washeluting with a gradient of acetonitrile in water containing 0.1% trifluoroacetic acid (5:95 to 100)

Sources & evidence

ORD record: ord-1db2567f59644905bca9ccb53ea02f1b
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902203B2

Reaction notes

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