Ethanol → 1-(4-Fluorobenzyl)-5-methanesulfonyl-2-(5-methyl-[1,2,4]oxadiazol-3-yl)indole
Reaction equation
[C:1]([C:3]1[N:4]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][CH:6]=2)#[N:2].Cl.[NH2:25]O.[OH-].[K+].[CH2:29]([OH:31])[CH3:30]>>[F:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:4]2[C:5]3[C:10](=[CH:9][C:8]([S:12]([CH3:15])(=[O:13])=[O:14])=[CH:7][CH:6]=3)[CH:11]=[C:3]2[C:1]2[N:25]=[C:29]([CH3:30])[O:31][N:2]=2)=[CH:22][CH:21]=1Participants
5
Conditions
- Temperature
- 100 °C
Procedure
A mixture of the compound obtained in Example 24 (1) (68 mg), hydroxylamine hydrochloride (22 mg), potassium hydroxide (18 mg) and ethanol (1 ml) was heated under reflux for 2 hours. After the insolubles were filtered off, the reaction mixture was concentrated under reduced pressure. A mixture of the resulting residue and dimethylacetamide dimethylacetal (1 ml) was stirred at 100° C. for 1 hour. Water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 50 mg of the desired product as a white crystal.
Workup
- temperaturewas heated
- temperatureunder reflux for 2 hours
- filtrationAfter the insolubles were filtered off
- concentrationthe reaction mixture was concentrated under reduced pressure
- additionA mixture of the resulting residue and dimethylacetamide dimethylacetal (1 ml)
- additionWater was added
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-df16cd957b9742c8a68b579f24a7ff3b
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06875770B2
Reaction notes
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