Hexane → 8-Methyl-2-(4-(trimethylsilyl)but-3-ynyl)-imidazo[1,2-a]pyridine

HRID 334566

Reaction equation

[CH3:1][Si:2]([CH3:7])([CH3:6])[C:3]#[C:4][CH3:5].[Li]CCCC.CCCCCC.Cl[CH2:20][C:21]1[N:22]=[C:23]2[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][N:24]2[CH:30]=1>C1COCC1>[CH3:29][C:28]1[C:23]2[N:24]([CH:30]=[C:21]([CH2:20][CH2:5][C:4]#[C:3][Si:2]([CH3:7])([CH3:6])[CH3:1])[N:22]=2)[CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of trimethyl(prop-1-ynyl)silane (259 mg, 2.31 mmol) in THF (7.5 mL) at −78° C. was added n-BuLi 2.5M in hexane (1.1 mL, 2.8 mmol). After 90 min at −78° C. 2-(chloromethyl)-8-methyl-imidazo[1,2-a]pyridine (500 mg, 2.8 mmol) in THF (5 mL) was added dropwise. The solution became blue-green at −78° C. The solution was stirred at −78° C. for an additional 1 h. The reaction was quenched with water and the solvent was removed under reduced pressure. The crude product was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM/MeOH from 100/0 to 99/1 as eluent) to afford 590 mg of 8-methyl-2-(4-(trimethylsilyl)but-3-ynyl)-imidazo[1,2-a]pyridine (Yield: 100%) as an yellow oil.

Workup

custombecame blue-green at −78° C
customThe reaction was quenched with water
customthe solvent was removed under reduced pressure
customThe crude product was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM/MeOH from 100/0 to 99/1 as eluent)

Sources & evidence

ORD record: ord-2e6d72e0b3334e52a9cd353e1ac45238
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883826B2

Linked notes

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