2-Bromo-6-(fluoromethyl)pyridine → 7-Chloro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-1-methyl-1H-benzo[d]imidazole

HRID 422441Notes

Reaction equation

HRID 422441 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][F:9])[N:3]=1.[CH2:10]([C:14]1[N:18]([CH3:19])[C:17]2[C:20]([Cl:24])=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]=1)[CH2:11][C:12]#[CH:13]>>[Cl:24][C:20]1[C:17]2[N:18]([CH3:19])[C:14]([CH2:10][CH2:11][C:12]#[C:13][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][F:9])[N:3]=3)=[N:15][C:16]=2[CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 860868842-(but-3-ynyl)-7-chloro-1-methyl-1H-benzo[d]imidazole

Product 1

HCID 665981927-Chloro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-1-methyl-1H-benzo[d]imidazole

Procedure

The title compound was prepared in accordance with the general method of Example 190(F), from 2-bromo-6-(fluoromethyl)pyridine (30 mg, 0.16 mmol) and 2-(but-3-ynyl)-7-chloro-1-methyl-1H-benzo[d]imidazole (35 mg, 0.16 mmol). The crude residue was purified over silicagel chromatography (prepacked 10 g silicagel column, DCM/MeOH: from 100/0 to 99/1 as eluent) to afford 43 mg of a light brown solid. The resulting solid was triturated into isopropyl ether to give 6 mg of 7-chloro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-1-methyl-1H-benzo[d]imidazole (Yield: 10%) as white solid.

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 10 g silicagel column, DCM/MeOH: from 100/0 to 99/1 as eluent)

Sources & evidence

ORD record
ord-92755570d79b4bb79a98c6b00cb28ed7
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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