2-Iodothiophene → HCID 18760182, compound

HRID 432690Notes

Reaction equation

[O:1]([C:8]1[C:17]2[N:18]=[CH:19][N:20]([CH2:21][CH2:22][O:23][CH2:24][C:25]#[CH:26])[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:28]1[S:29][CH:30]=[CH:31][CH:32]=1>>[O:1]([C:8]1[C:17]2[N:18]=[CH:19][N:20]([CH2:21][CH2:22][O:23][CH2:24][C:25]#[C:26][C:32]3[CH:31]=[CH:30][S:29][CH:28]=3)[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 189212-Iodothiophene

HCID 18760197HCID 18760197, compound

Product 1

HCID 18760182HCID 18760182, compoundYield 42.4%

Procedure

Using the general method of Example 3 Part A, 4-phenoxy-1-[2-(prop-2-ynyloxy)ethyl]-1H-imidazo[4,5-c]quinoline (10 g, 29.4 mmol) was reacted with 2-iodothiophene (3.6 mL, 32.3 mmol). The glassy solid obtained from purification by chromatography over silica gel (98/2 dichloromethane/methanol) was triturated with ether to provide 5.3 g of 4-phenoxy-1-{2-[(3-thien-3-ylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinoline as a gray powder.

Workup

customThe glassy solid obtained from purification by chromatography over silica gel (98/2 dichloromethane/methanol)
customwas triturated with ether

Sources & evidence

ORD record: ord-5f34972a779941c08a3e8ad7bb0df256
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06664260B2

Reaction notes

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