Toluene → HCID 59641868, compound

HRID 2250479Notes

Reaction equation

Br[C:2]1[N:3]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:4](Br)=[C:5]([Br:7])[N:6]=1.C1(B(O)O)C=CC=CC=1.[C:26]1(C)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH3:33][O:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1>C(=O)([O-])[O-].[Na+].[Na+]>[Br:7][C:5]1[N:6]=[C:2]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:3]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:4]=1[C:38]1[CH:39]=[CH:40][C:35]([O:34][CH3:33])=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Through a mixture of 2,4,5-tribromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole [Lipshutz et al. (Tet Lett 1992, 33, 5865-5868)] (3.75 g, 7.09 mmol) and phenyl boronic acid (865 mg, 7.09 mmol) in 2 M aqueous sodium carbonate (7.09 mL) and a 5:1 mixture of toluene:methanol (168 mL) was bubbled nitrogen gas for 10 min. Palladium tetrakis triphenylphosphine (820 mg, 0.71 mmol) was added to the mixture that was then heated under nitrogen at 90° C. for 2 h. To the reaction mixture was added 4-methoxy phenyl boronic acid (1.19 g, 7.80 mmol) and another 2 M aqueous sodium carbonate (7 mL). The mixture was refluxed 4 h. The mixture was then concentated in vacuo and purified by flash column chromatography (silica gel, 20% ethyl acetate in hexanes) to provide the title compound as an oil (1.26 g, 39% yield). MS m/e 461; HPLC retention time 4.31 min (Method A).

Workup

custommethanol (168 mL) was bubbled nitrogen gas for 10 min
temperatureThe mixture was refluxed 4 h
custompurified by flash column chromatography (silica gel, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-117b03366f5649d0a8762a9b09351bfe
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317032B2

Reaction notes

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