2-Iodopyridine → Benzimidazole

HRID 422450Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([C:12]1[N:16]([CH:17]([CH3:19])[CH3:18])[C:15]2[CH:20]=[CH:21][CH:22]=[CH:23][C:14]=2[N:13]=1)[CH2:9][C:10]#[CH:11]>>[CH:17]([N:16]1[C:15]2[CH:20]=[CH:21][CH:22]=[CH:23][C:14]=2[N:13]=[C:12]1[CH2:8][CH2:9][C:10]#[C:11][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)([CH3:19])[CH3:18].[NH:13]1[C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[N:16]=[CH:12]1

Participants

Reactant 2

HCID 2211262-Iodopyridine

HCID 86086904HCID 86086904, compound

Product 2

HCID 5798BenzimidazoleYield 41%

HCID 66598196HCID 66598196, compound

Procedure

The title compound was prepared in accordance with the general method of Example 192(A), from 2-iodopyridine (81 mg, 0.39 mmol) and 2-(but-3-ynyl)-1-isopropyl-1H-benzo[d]imidazole (84 mg, 0.39 mmol). The crude residue was purified over silicagel chromatography (prepacked 5 g silicagel column, DCM/MeOH: from 100/0 to 96/4 as eluent) to afford 47 mg of 1-isopropyl-2-(pyridin-2-yl)but-3-ynyl)-1H-benzo[d]imidazole as a light brown oil (Yield: 41%).

Workup

customThe crude residue was purified over silicagel chromatography (prepacked 5 g silicagel column, DCM/MeOH: from 100/0 to 96/4 as eluent)

Sources & evidence

ORD record: ord-f0f8cf6e13b44288a03fbbeafe805c92
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101637B2

Reaction notes

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