Benzene → 3,5-dimethyl-7-(3-methylbutoxy)-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester
Reaction equation
[H-].[Na+].C1C=CC=CC=1.Cl[C:10]1[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([CH3:21])[N:13]=[C:12]2[N:22]([CH3:25])[CH:23]=[N:24][C:11]=12.[CH3:26][CH:27]([CH3:31])[CH2:28][CH2:29][OH:30]>>[CH3:25][N:22]1[C:12]2=[N:13][C:14]([CH3:21])=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([O:30][CH2:29][CH2:28][CH:27]([CH3:31])[CH3:26])=[C:11]2[N:24]=[CH:23]1Participants
Procedure
0.3 g. of sodium hydride are suspended in 100 ml. of anhydrous benzene. The mixture is heated with stirring at reflux temperature while 8.8 g. of 3-methylbutane-1-ol are dropped in. After the addition is completed, the mixture is refluxed for an additional 10 hours. After this time 25.3 g. of 7-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester obtained in Example 2 c are added and refluxing is continued for 12 hours. The inorganic precipitate is filtered off and the solvent removed in vacuo. The oily residue is dissolved in 50 ml. of ether and, on cooling, 3,5-dimethyl-7-(3-methylbutoxy)-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester is obtained. Yield 24.3 g. (80%), m.p. 64°-66° (diethyl ether).
Workup
- temperatureThe mixture is heated
- temperatureat reflux temperature while 8.8 g
- additionAfter the addition
- temperaturethe mixture is refluxed for an additional 10 hours
- temperaturerefluxing
- filtrationThe inorganic precipitate is filtered off
- customthe solvent removed in vacuo
- dissolutionThe oily residue is dissolved in 50 ml
- temperatureof ether and, on cooling
Sources & evidence
- ORD record
- ord-c0c71e1410904babb8c5c119fb152ede
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04088654
Reaction notes
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