Sodium Chloride → HCID 57616207, compound
Reaction equation
[C@@H:1]1([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:21])[CH:19]=3)[N:14]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[CH:13]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].[CH2:38](Br)[CH3:39].[Cl-].[Na+]>C(#N)C>[CH2:38]([O:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:14]2[C:15]3[C:20](=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[C:12]([C@@H:1]3[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]3[OH:3])=[CH:13]2)=[CH:28][CH:27]=1)[CH3:39]Participants
7
Conditions
- Temperature
- 40 °C
Procedure
To a mixture of 3-(β-D-glucopyranosyl)-1-(4-hydroxy-benzyl)-5-methyl-1H-indole (50 mg), cesium carbonate (82 mg) and sodium iodide (19 mg) in acetonitrile (1 mL) was added ethyl bromide (41 mg), and the mixture was stirred at 40° C. for 3 days. The reaction mixture was poured into 15% aqueous sodium chloride solution, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (21 mg).
Workup
- extractionthe resulting mixture was extracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous sodium sulfate
- customthe solvent was removed under reduced pressure
- customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)
Sources & evidence
- ORD record
- ord-a7225f8948eb498685a6036c6b489dc8
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750145B2
Reaction notes
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