2-Bromo-6-(fluoromethyl)pyridine → HCID 66598428, compound

HRID 1189314Notes

Reaction equation

HRID 1189314 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][F:9])[N:3]=1.[CH2:10]([O:17][C:18]1[C:19]2[N:20]([CH:24]=[C:25]([CH2:27][CH2:28][C:29]#[CH:30])[N:26]=2)[CH:21]=[CH:22][CH:23]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([O:17][C:18]1[C:19]2[N:20]([CH:24]=[C:25]([CH2:27][CH2:28][C:29]#[C:30][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][F:9])[N:3]=3)[N:26]=2)[CH:21]=[CH:22][CH:23]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 860867788-(Benzyloxy)-2-(but-3-ynyl)-imidazo[1,2-a]pyridine

Product 1

HCID 66598428HCID 66598428, compoundYield 6%

Procedure

The title compound was prepared in accordance with the general method of Example 190(F), from 2-bromo-6-(fluoromethyl)pyridine (82 mg, 0.43 mmol) and 8-(benzyloxy)-2-(but-3-ynyl)-imidazo[1,2-a]pyridine (119 mg, 0.43 mmol). The crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column, Cyclohexane/AcOEt: from 100/0 to 60/40 as eluent) to afford 10 mg of 8-(benzyloxy)-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-imidazo[1,2-a]pyridine (Yield: 6%) beige solid (Mp=92-94° C.)

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column, Cyclohexane/AcOEt: from 100/0 to 60/40 as eluent)

Sources & evidence

ORD record
ord-aba1040d27e445419fe8e325d4a5289b
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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