2-Bromo-6-(fluoromethyl)pyridine → 8-Chloro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-imidazo[1,2-a]pyridine

HRID 334822Notes

Reaction equation

HRID 334822 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]2[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][N:8]2[CH:14]=1)[CH2:2][C:3]#[CH:4].Br[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][F:23])[N:17]=1>>[Cl:13][C:12]1[C:7]2[N:8]([CH:14]=[C:5]([CH2:1][CH2:2][C:3]#[C:4][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][F:23])[N:17]=3)[N:6]=2)[CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 860869362-(But-3-ynyl)-8-chloro-imidazo[1,2-a]pyridine

Product 1

HCID 115006098-Chloro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-imidazo[1,2-a]pyridineYield 55%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-(but-3-ynyl)-8-chloro-imidazo[1,2-a]pyridine (500 mg, 2.44 mmol, Example 255(B)) and 2-bromo-6-(fluoromethyl)pyridine (487 mg, 2.57 mmol, Example 190(E)). The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 420 mg (1.34 mmol, 55%) of 8-chloro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-imidazo[1,2-a]pyridine as a slightly yellow solid (M.P.=73-74.5° C.).

Workup

  1. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-7dfab1da60fc4c528763e51b616e1859
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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