o-Iodonitrobenzene → 2-Methyl-1-(pyridin-2-yl)-1H-benzimidazole

HRID 1931273Notes

Reaction equation

HRID 1931273 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)(=O)[CH3:12]>>[CH3:12][C:11]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=1

Participants

3

Reactant 2

HCID 69115o-IodonitrobenzeneHCID 729292-Acetamidopyridine

Product 1

HCID 227366432-Methyl-1-(pyridin-2-yl)-1H-benzimidazoleYield 38.2%

Procedure

Method A applied to 1-iodo-2-nitrobenzene (125 mg, 0.5 mmol) and 2-acetamido-pyridine (82 mg, 0.6 mmol) yielded the title compound as yellowy oil (40 mg, 38%). 1H NMR (DMSO) δ 2.74 (s, 3H), 7.42-7.49 (m, 2H), 7.56 (d, 1H), 7.70 (dd, 1H), 7.78-7.88 (m, 2H), 8.22 (dd, 1H), 8.77 (dd, 1H); 13C NMR δ 13.6, 112.0, 116.1, 121.0, 124.7, 124.9, 133.0, 135.2, 140.1, 147.2, 150.0, 151.7.

Sources & evidence

ORD record
ord-00e9682a48db4a13a0ab5fb3a63d39c1
Source dataset
uspto-grants-2012_05
Patent number
US08188282B2

Reaction notes

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