2-Iodopyridine → HCID 66598376, compound

HRID 1189272Notes

Reaction equation

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

Participants

Reactant 2

HCID 2211262-Iodopyridine

HCID 86086725HCID 86086725, compound

Product 1

HCID 66598376HCID 66598376, compoundYield 27.8%

Procedure

The title compound was prepared in accordance with the general method of Example 192(A), from 2-iodopyridine (74 mg, 0.36 mmol) and 2-(but-3-ynyl)-5-fluoro-1-methyl-1H-benzo[d]imidazole (73 mg, 0.36 mmol). The crude residue was purified over silicagel chromatography (prepacked 2 g silicagel column, DCM/MeOH: from 100/0 to 98/2 as eluent) to afford 28 mg of 5-fluoro-1-methyl-2-(4-(pyridin-2-yl)but-3-ynyl)-1H-benzo[d]imidazole as a orange oily solid (Yield: 27%).

Workup

customThe crude residue was purified over silicagel chromatography (prepacked 2 g silicagel column, DCM/MeOH: from 100/0 to 98/2 as eluent)

Sources & evidence

ORD record: ord-1e2ab1cbcc8645e9bb2a6c8bb1dfa17f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674106B2

Reaction notes

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