6-imidazol-1-yl-2-(4-iodo-2-methoxy-pyridin-3-yl)-4-methyl-1H-benzimidazole → 3-(6-Imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-4-iodo-1H-pyridin-2-one

HRID 1354602Notes

Reaction equation

[N:1]1([C:6]2[CH:7]=[C:8]([CH3:24])[C:9]3[N:13]=[C:12]([C:14]4[C:15]([O:21]C)=[N:16][CH:17]=[CH:18][C:19]=4[I:20])[NH:11][C:10]=3[CH:23]=2)[CH:5]=[CH:4][N:3]=[CH:2]1>Cl.C(OCC)(=O)C>[N:1]1([C:6]2[CH:7]=[C:8]([CH3:24])[C:9]3[N:13]=[C:12]([C:14]4[C:15](=[O:21])[NH:16][CH:17]=[CH:18][C:19]=4[I:20])[NH:11][C:10]=3[CH:23]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

The suspension of 6-imidazol-1-yl-2-(4-iodo-2-methoxy-pyridin-3-yl)-4-methyl-1H-benzimidazole in 1 N HCl (6 mL) was heated to 70° C. for 3 days, cooled to room temperature, and diluted with ethyl acetate. After extraction, the combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (1% NH4OH/10% MeOH/CH2Cl2) to yield the title compound (78 mg, 81%) as a solid. 1H NMR (300 MHz, CD3OD) δ 8.12 (1H, s), 7.58 (2H, s), 7.29–7.31 (2H, m), 7.16 (1H, s), 7.01 (1H, J=6.8 Hz), 2.66 (3H, s). LCMS (M+H)+ m/z 418 (t=0.75 min.)

Workup

temperaturecooled to room temperature
extractionAfter extraction
washthe combined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified by flash chromatography (1% NH4OH/10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-3b29ba52caad4150806f53584c471b58
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223757B2

Reaction notes

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