Benzyl Bromide → 2-Benzyloxymethyl-1-(3,5-dichloro-benzyl)-1H-imidazole

HRID 2101510Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][OH:14].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:14][CH2:13][C:9]1[N:8]([CH2:7][C:6]2[CH:15]=[C:16]([Cl:18])[CH:17]=[C:4]([Cl:3])[CH:5]=2)[CH:12]=[CH:11][N:10]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To NaH in DMF, was added [1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-methanol (see Example 1) in DMF. The reaction mixture was stirred at 40° C. for 30 min and benzyl bromide was dropwise added. The reaction mixture was stirred at 40° C. for another 3 h. The mixture was diluted with EtOAc and washed with water, 1N HCl and saturated NaHCO3. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using CH2Cl2:MeOH 98:2 as an eluent to afford the title compound (7 mg, 5%); MS m/z 347 [C18H16Cl2N2O+H]+.

Workup

stirringThe reaction mixture was stirred at 40° C. for another 3 h
washwashed with water, 1N HCl and saturated NaHCO3
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated
customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record: ord-3046409271b84e10b6d14775e033c287
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572921B2

Reaction notes

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