Iodobenzene → HCID 22254458, compound

HRID 433990Notes

Reaction equation

[CH2:1]([C:9]1[N:10]([CH2:22][CH2:23][O:24][CH2:25][C:26]#[CH:27])[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].I[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:1]([C:9]1[N:10]([CH2:22][CH2:23][O:24][CH2:25][C:26]#[C:27][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[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 11575Iodobenzene

HCID 22254484HCID 22254484, compound

Product 1

HCID 22254458HCID 22254458, compoundYield 71.7%

Procedure

Using the general method of Example 12 Part A, 2-octyl-1-[2-(prop-2-ynyloxy)ethyl]-1H-imidazo[4,5-c]quinoline (4.84 g, 13.32 mmol) was reacted with iodobenzene (1.7 mL, 14.65 mmol) at 40° C. After 45 minutes the reaction was judged complete. The volatiles were removed under reduced pressure and the resulting oil purified by chromatography over silica gel (98/2 (dichloromethane/methanol) to provide 4.2 g of 2-octyl-1-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinoline as a pale yellow solid.

Workup

customThe volatiles were removed under reduced pressure
customthe resulting oil purified by chromatography over silica gel (98/2 (dichloromethane/methanol)

Sources & evidence

ORD record: ord-63c6625b7f754978ad764883f1112bd0
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06670372B2

Reaction notes

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