Imidazole → 2-(4-Hydroxy-phenyl)-7-imidazol-1-ylmethyl-benzofuran-5-ol

HRID 1835979Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of benzyl bromide 4 (0.070 g, 0.215 mmole) in 10 mL DMF was added imidazole (0.030 g, 0.437 mmole). After stirring at 60° C. for 3 hours, the reaction mixture was poured into water and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 9:1) to afford 0.059 g (88%) of imidazole 16 as a light tan solid: Mp=269-271° C.; 1H NMR (DMSO-d6) δ 9.88 (s, 1 H), 9.24 (s, 1 H), 7.88 (s, 1 H), 7.72 (d, 2 H, J=8.6 Hz), 7.26 (s, 1 H), 7.04 (s, 1 H), 6.93 (s, 1 H), 6.88 (d, 2 H, J=8.7 Hz), 6.83 (d, 1 H, J=2.3 Hz), 6.50 (d, 1 H, J=2.3 Hz), 5.46 (s, 2 H); MS 305 (M−H)−

Workup

extractionextracted with ethyl acetate
washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
dry with materialdried with magnesium sulfate
concentrationThe organic phases were concentrated
customchromatographed with silica gel (hexanes:ethyl acetate, 9:1)

Sources & evidence

ORD record: ord-9507071d6c1c433d8ccba93cf65b43d5
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06774248B2

Reaction notes

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