2-Bromo-6-(fluoromethyl)pyridine → HCID 66597939, compound

HRID 1189257Notes

Reaction equation

HRID 1189257 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[CH:20]=[C:21]([F:25])[CH:22]=[C:23]([F:24])[C:16]=2[N:15]=1)[CH2:11][C:12]#[CH:13]>>[F:24][C:23]1[C:16]2[N:15]=[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:18]([CH3:19])[C:17]=2[CH:20]=[C:21]([F:25])[CH:22]=1

Participants

3

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 86086898HCID 86086898, compound

Product 1

HCID 66597939HCID 66597939, compound

Procedure

The title compound was prepared in accordance with the general method of Example 190(F), from 2-bromo-6-(fluoromethyl)pyridine (109 mg, 0.57 mol) and 2-(but-3-ynyl)-4,6-difluoro-1-methyl-1H-benzo[d]imidazole (126 mg, 0.57 mmol). The crude residue was purified over silicagel chromatography (prepacked 25 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 dissolved in Dioxane and 0.5N HCl in dioxan was added (0.14 mL, 0.07 mmol). A green solid was formed and it was collected by filtration and washed with AcOEt. The chlorhydrate salt was dissolved in MeOH, neutralized by saturated NaHCO3. The aqueous layer was extracted twice with AcOEt. The organic layer was dried over MgSO4 and the solvent removed under reduced pressure to afford 9 mg of 4,6-difluoro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-1-methyl-1H-benzo[d]imidazole (Yield: 5%) as purple oily solid (Mp=103° C.-104° C.).

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM/MeOH: from 100/0 to 99/1 as eluent)

Sources & evidence

ORD record
ord-7b1b397f36864b39a473de7860157d54
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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