2-Bromo-6-(fluoromethyl)pyridine → HCID 66597939, compound
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]=1Participants
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 mmol) 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
- 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-c317345fac3d4f77b8c5417019d6066b
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101637B2
Reaction notes
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