N-bromobutanimide → 2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carbonitrile

HRID 646839Notes

Reaction equation

[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]#[N:13])[N:9]=[CH:8]1.C1C(=O)N([Br:23])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O.CC(N=NC(C#N)(C)C)(C#N)C>[Br:23][C:8]1[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:15])([CH3:14])[CH3:1])[CH:11]=[C:10]([C:12]#[N:13])[N:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile (0.70 g, 3.1 mmol) (as prepared in the previous step) in CCl4 (10 mL) was added NBS (0.61 g, 3.4 mmol) and AIBN (2 mg, catalytic), and the mixture heated at 60° C. for 4 h. The reaction was diluted with EtOAc (30 mL) and washed with NaHCO3 (2×30 mL) and brine (30 mL) and the organic layer was dried over Na2SO4 and then concentrated. The title compound was eluted from a 20-g SPE cartridge (silica) with 30% EtOAc/hexane to give 0.73 g (77%) of a yellow solid. Mass spectrum (CI(CH4), m/z) Calcd. for C10H16BrN3OSi, 302.0/304.0 (M+H), found 302.1/304.1.

Workup

washwashed with NaHCO3 (2×30 mL) and brine (30 mL)
dry with materialthe organic layer was dried over Na2SO4
concentrationconcentrated
washThe title compound was eluted from a 20-g SPE cartridge (silica) with 30% EtOAc/hexane

Sources & evidence

ORD record: ord-4a2645829b604694a4e19e0c22157731
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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