2-Bromo-4-nitro-1H-imidazole → HCID 68549369, compound

HRID 1446089Notes

Reaction equation

HRID 1446089 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:11])[CH2:10][O:9]2)=[CH:4][CH:3]=1.Br[C:13]1[NH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][N:17]=1>C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH3:11])[O:9][C:13]3=[N:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][N:17]3[CH2:10]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 477542-Bromo-4-nitro-1H-imidazoleHCID 1507022-(4-Bromophenyl)-2-methyloxirane

Product 1

HCID 68549369HCID 68549369, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-(4-Bromo-phenyl)-2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole was synthesized according to the scheme shown in FIG. 6. 2-(4-Bromo-phenyl)-2-methyl-oxirane (213 mg, 1 mmol), 2-bromo-5-nitroimidazole (191 mg, 1 mmol) and triethylamine (0.4 mL) were stirred in a sealed tube at 80° C. for 6 hours Column chromatography (EtOAc/Hexanes, v/v, 1/1 to 3/1) gave 330 mg yellow solid. The solid was dissolved in 5 mL DMF with Cs2CO3 (780 mg, 2.4 mmol). The resulting mixture was stirred at 50° C. for 24 hours and then partitioned in EtOAc/water (200 mL, 1/1, v/v). The organic layer was washed with brine and dried over Na2SO4 Column chromatography (EtOAc/Hexanes, v/v, 1/1 to 3/1) gave the titled compound (178 mg, 55% yield in two steps) as yellow solid. ESI MS m/z 324, 326 (M+H). 1H NMR (400 MHz, Acetone-d6) δ 7.66 (s, 1H), 7.76 (s, 1H), 7.52 (d, J=8.2 Hz, 2H), 7.41 (d, J=8.2 Hz, 2H), 4.58 (d, J=10.8 Hz, 1H), 4.47 (d, J=10.8 Hz, 1H), 1.89 (s, 3H).

Sources & evidence

ORD record
ord-230d895dc7f6408e88403b997dae5dbe
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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