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 II a 1H-imidazo[4,5-c]quinolin-1-yl alcohol of Formula XVII is alkylated with an iodide of Formula XVI to provide a 1H-imidazo[4,5-c]quinolin-1-yl ether of Formula XVIII. The alcohol of Formula XVII is 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. After the addition is complete the reaction is stirred at an elevated temperature (˜100° C.). Many compounds of Formula XVII are known, see for example, Gerster, U.S. Pat. No. 4,689,338; others can readily be prepared using known synthetic routes, see for example, Gerster et al., U.S. Pat. No. 5,605,899 and Gerster, U.S. Pat. No. 5,175,296.
Sources & evidence
- ORD record
- ord-11a26cf0976449fcbdaaa9f8c4a0228a
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06683088B2
Reaction notes
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