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

HRID 1931270Notes

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

Reactant 2

HCID 69115o-Iodonitrobenzene

HCID 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 brown solid (40 mg, 38%). mp 121-123° C. 1H NMR (DMSO) δ 2.69 (s, 3H), 7.36-7.46 (m, 2H), 7.53 (d, J=7.4 Hz, 1H), 7.68 (dd, J=7.6, 4.7Hz, 1H), 7.77 (d, J=7.6Hz, 1H), 7.81 (d, J=7.9Hz, 1H), 8.21 (dd, J=7.9, 7.6Hz, 1H), 8.75 (d, J=4.7Hz); 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, 157.9. HRMS (FAB): cal. for C13H12N3 [M+H+]: 210.1031; found: 210.1025.

Sources & evidence

ORD record: ord-325990a1b1c740a38d3c2e62125e7051
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188282B2

Reaction notes

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