Azobisisobutyronitrile → Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 646903Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=1)=[O:4].C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([Br:25])[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:16])([CH3:15])[CH3:17])[CH:9]=1)=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carboxylic acid methyl ester (0.43 g, 1.6 mmol) (as prepared in the previous step) in CCl4 (10 mL) was added NBS (0.30 g, 1.7 mmol) and AIBN (cat) and the mixture heated at 60° C. for 4 h. The reaction was diluted with EtOAc (30 ml) and washed with satd NaHCO3 (2×30 mL) and brine (30 mL) and the organic layer concentrated. The title compound was eluted from a 20-g SPE cartridge (silica) with 50% EtOAc/hexane to give 0.40 g (71%) of a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C11H19BrN2O3Si, 335.0/337.0 (M+H), found 335.0/337.0.

Workup

washwashed with satd NaHCO3 (2×30 mL) and brine (30 mL)
concentrationthe organic layer concentrated
washThe title compound was eluted from a 20-g SPE cartridge (silica) with 50% EtOAc/hexane

Sources & evidence

ORD record: ord-a52b9d53558d4bab81687be988eab0ed
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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