4-Iodo-2-methoxynicotinaldehyde → 6-imidazol-1-yl-2-(4-iodo-2-methoxy-pyridin-3-yl)-4-methyl-1H-benzimidazole

HRID 1354601Notes

Reaction equation

[N:1]1([C:6]2[CH:11]=[C:10]([NH2:12])[C:9]([NH2:13])=[C:8]([CH3:14])[CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[I:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH3:23])[C:17]=1[CH:24]=O>CO>[N:1]1([C:6]2[CH:7]=[C:8]([CH3:14])[C:9]3[N:13]=[C:24]([C:17]4[C:18]([O:22][CH3:23])=[N:19][CH:20]=[CH:21][C:16]=4[I:15])[NH:12][C:10]=3[CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-imidazol-1-yl-3-methyl-benzene-1,2-diamine (175 mg, 0.93 mmol) in methanol (8 mL) was added a solution of 4-iodo-2-methoxy-pyridine-3-carbaldehyde (245 mg, 0.93 mmol) in methanol (5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1.5 h and then at room temperature for 2 h. After concentration, the residue was purified by flash column chromatography (10% MeOH/CH2Cl2) to give the title compound (291 mg, 60%). 1H NMR (300 MHz, CD3OD) δ 8.13 (1H, s), 7.98 (1H, d, J=5.4 Hz), 7.62 (1H, d, J=5.4 Hz), 7.59 (2H, s), 7.33 (1H, s), 7.16 (1H, s), 3.90 (3H, s), 2.67 (3H, s). LCMS (M+H)+ m/z 432 (t=0.99 min.).

Workup

waitat room temperature for 2 h
concentrationAfter concentration
customthe residue was purified by flash column chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-ecccb11a2c664aeca6ceb998b7df1ac4
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223757B2

Reaction notes

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