2-Amino-3-bromopyridine → 8-Bromo-2-(4-(trimethylsilyl)but-3-ynyl)-imidazo[1,2-a]pyridine

HRID 334785Notes

Reaction equation

HRID 334785 reaction equation
[Br:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.Br[CH2:10][C:11](=O)[CH2:12][CH2:13][C:14]#[C:15][Si:16]([CH3:19])([CH3:18])[CH3:17]>>[Br:1][C:2]1[C:3]2[N:4]([CH:10]=[C:11]([CH2:12][CH2:13][C:14]#[C:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:8]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8177002-Amino-3-bromopyridineHCID 860867691-Bromo-6-(trimethylsilyl)hex-5-yn-2-one2×

Product 1

HCID 665983208-Bromo-2-(4-(trimethylsilyl)but-3-ynyl)-imidazo[1,2-a]pyridineYield 61.3%

Procedure

The title compound was prepared in accordance with the general method of Example 223(D), from 3-bromopyridin-2-amine (280 mg, 1.60 mmol) and 1-bromo-6-(trimethylsilyl)hex-5-yn-2-one (compound 223(C), 870 mg, 3.5 mmol). The crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM/MeOH: from 100/0 to 98/2 as eluent) to afford 315 mg of 8-bromo-2-(4-(trimethylsilyl)but-3-ynyl)-imidazo[1,2-a]pyridine (Yield: 61%) as a yellow oil.

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM/MeOH: from 100/0 to 98/2 as eluent)

Sources & evidence

ORD record
ord-da3bb06cdf1f4b44b2350e2e40ecea5e
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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