5-Methylimidazo[1,2-a]pyridine → 5-(3-t-Butyldimethylsiloxypropyl)imidazo[1,2-a]pyridine

HRID 357011Notes

Reaction equation

[CH3:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>>[O:22]([CH2:21][CH2:20][CH2:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1)[Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

Reactant 3

HCID 1367405-Methylimidazo[1,2-a]pyridine

HCID 2724682Lithium diisopropylamide

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 702056155-(3-t-Butyldimethylsiloxypropyl)imidazo[1,2-a]pyridineYield 64.8%

Procedure

Using 13.22 g (100 mmol) of 5-methylimidazo[1,2-a]pyridine, 50 ml (100 mmol) of a 2M lithium diisopropylamide solution (produced by Aldrich Company) and 23.92 g (100 mmol) of 1-bromo-2-t-butyldimethylsiloxyethane, the same procedure as in Reference Example 3 was followed, to yield 18.81 g (64.8%, yellow oily substance) of 5-(3-t-butyldimethylsiloxypropyl)imidazo[1,2-a]pyridine.

Sources & evidence

ORD record: ord-d009cf1a6ea24a8fb641d20d63a5f52b
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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