3,5-Difluoropyridin-2-amine → 6,8-Difluoro-2-(4-(trimethylsilyl)but-3-ynyl)-imidazo[1,2-a]pyridine

HRID 334790Notes

Reaction equation

HRID 334790 reaction equation
[F:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.Br[CH2:11][C:12](=O)[CH2:13][CH2:14][C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18]>>[F:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]2[N:4]([CH:11]=[C:12]([CH2:13][CH2:14][C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:9]=2)[CH:5]=1

Participants

3

Reactant 2

HCID 27832383,5-Difluoropyridin-2-amineHCID 860867691-Bromo-6-(trimethylsilyl)hex-5-yn-2-one2×

Product 1

HCID 665985106,8-Difluoro-2-(4-(trimethylsilyl)but-3-ynyl)-imidazo[1,2-a]pyridineYield 49.1%

Procedure

The title compound was prepared in accordance with the general method of Example 223(D), from 3,5-difluoropyridin-2-amine (492 mg, 3.78 mmol) and 1-bromo-6-(trimethylsilyl)hex-5-yn-2-one (compound 223(C), 1.87 mg, 7.56 mmol). The crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column, from DCM/Cyclohexane: 70/30 to DCM/MeOH: 95/5 as eluent) to afford 517 mg of 6,8-difluoro-2-(4-(trimethylsilyl)but-3-ynyl)-imidazo[1,2-a]pyridine (Yield: 49%) as a brown oil.

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column, from DCM/Cyclohexane: 70/30 to DCM/MeOH: 95/5 as eluent)

Sources & evidence

ORD record
ord-28e5ab42e4ff4a43bb9c71a6bbce1e81
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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