4-Chlorophenylboronic acid → HCID 86303660, compound

HRID 1476689Notes

Reaction equation

HRID 1476689 reaction equation
ClC1C=CC(B(O)O)=CC=1.BrC1N=CNC=1.Br[C:18]1[N:19]=[CH:20][N:21]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:22]=1.[O:30]1[CH:34]=[CH:33][CH:32]=[C:31]1B(O)O>>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([N:21]2[CH:22]=[C:18]([C:31]3[O:30][CH:34]=[CH:33][CH:32]=3)[N:19]=[CH:20]2)=[CH:24][CH:25]=1

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 2734357Furan-2-boronic acidHCID 66520703HCID 66520703, compoundHCID 178418934HCID 178418934, compound

Product 1

HCID 86303660HCID 86303660, compoundYield 12%

Procedure

The procedure described above for Formula Ic-iii in Example 16 was followed, starting from 4-chloro-phenylboronic acid and 4-bromo-1H-imidazole, to prepare 4-bromo-1-(4-chlorophenyl)-1H-imidazole, which was then reacted with furan-2-ylboronic acid to prepare the desired 1-(4-chlorophenyl)-4-(furan-2-yl)-1H-imidazole (15 mg, 0.061 mmol, yield 12%) as an off-white solid. The HPLC purity of the final product was 95.45%. LC-MS [M+H] 245 (C13H9ClN2O+H expected 245.04). The 1H-NMR spectra was in accordance with the chemical structure.

Sources & evidence

ORD record
ord-8244ffce8d4d424c9c91257669a115bf
Source dataset
uspto-grants-2016_08
Patent number
US09402397B2

Reaction notes

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