Propargyl bromide → HCID 22254484, compound

HRID 1611775Notes

Reaction equation

[CH2:1]([C:9]1[N:10]([CH2:22][CH2:23][OH:24])[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:25](Br)[C:26]#[CH:27]>>[CH2:1]([C:9]1[N:10]([CH2:22][CH2:23][O:24][CH2:27][C:26]#[CH:25])[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Reactant 2

HCID 7842Propargyl bromide

HCID 222545012-Octyl-1H-imidazo[4,5-c]quinoline-1-ethanol

Product 1

HCID 22254484HCID 22254484, compoundYield 90.3%

Procedure

Using the general method of Example 1 Part A, 2-(2-octyl-1H-imidazo[4,5-c]quinolin-1-yl)ethanol (4.8 g, 14.75 mmol) was reacted with propargyl bromide (80% in toluene, 4.93 mL, 44.25 mmol) to provide 4.84 g of 2-octyl-1-[2-(prop-2-ynyloxy)ethyl]-1H-imidazo[4,5-c]quinoline as a brown solid.

Sources & evidence

ORD record: ord-6a2754be38954c4f98a421cd9b975944
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06989389B2

Reaction notes

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