2-Bromo-6-(fluoromethyl)pyridine → HCID 66598150, compound

HRID 334783Notes

Reaction equation

HRID 334783 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:15]=[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]2[CH:23]=1)[CH2:11][C:12]#[CH:13]>>[F:22][C:19]1[CH:20]=[CH:21][C:16]2[N:17]([CH:23]=[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]=2)[CH:18]=1

Participants

3

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 860867362-(But-3-ynyl)-6-fluoro-imidazo[1,2-a]pyridine

Product 1

HCID 66598150HCID 66598150, compound

Procedure

The title compound was prepared in accordance with the general method of Example 190(F), from 2-bromo-6-(fluoromethyl)pyridine (220 mg, 1.10 mol) and 2-(but-3-ynyl)-6-fluoro-imidazo[1,2-a]pyridine (220 mg, 1.14 mmol). The crude residue was purified over C18 chromatography (prepacked 35 g silicagel column, H2O/CH3CN: from 95/5 to 55/45 as eluent) to afford 155 mg of 6-fluoro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)H-imidazo[1,2-a]pyridine (Yield: 46%) as a white powder (Mp=140-141.8° C.).

Workup

  1. customThe crude residue was purified over C18 chromatography (prepacked 35 g silicagel column, H2O/CH3CN: from 95/5 to 55/45 as eluent)

Sources & evidence

ORD record
ord-17ecffd3e3fc4557acf12b56c194db2a
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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