Iodide Ion → 1H-imidazo[4,5-c]quinolin-1-yl ether
Reaction equation
[N:1]1([OH:14])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.[I-]>>[N:1]1([O:14][N:1]2[C:13]3[C:12]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[N:6]=[CH:5][C:4]=3[N:3]=[CH:2]2)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1Participants
Procedure
In step (3) of Reaction Scheme IV a 1H-imidazo[4,5-c]quinolin-1-yl alcohol of Formula XXXII is alkylated with an iodide of Formula XXXI to provide a 1H-imidazo[4,5-c]quinolin-1-yl ether of Formula XXXIII. The 1H-imidazo[4,5-c]quinolin-1-yl alcohol of Formula XXXII represents a subset of the compounds represented by Formula XXI in Reaction Scheme III. The compound of Formula XXXII can be prepared using the procedure described for the synthesis of the compound of Formula XXI in Reaction Scheme III. In step (3), the alcohol of Formula XXXII can be reacted with sodium hydride in a suitable solvent such as N,N-dimethylformamide to form an alkoxide. The iodide is added to the alkoxide solution at ambient temperature and then stirred at an elevated temperature (approximately 100° C.).
Sources & evidence
- ORD record
- ord-13e1173e2eb24de8b59ed4e5730b6a78
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09107958B2
Reaction notes
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