Lithium hydroxide, monohydrate → 1-(5-(4-Methylpyridin-2-yl)pyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acid
Reaction equation
O.[OH-].[Li+].[CH3:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[CH:12]=[N:13][C:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26]([O:28]C)=[O:27])[CH:24]=4)[C:19]([S:30][CH3:31])=[CH:18]3)=[N:15][CH:16]=2)[CH:6]=1>C1COCC1.O>[CH3:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[CH:16]=[N:15][C:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26]([OH:28])=[O:27])[CH:24]=4)[C:19]([S:30][CH3:31])=[CH:18]3)=[N:13][CH:12]=2)[CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Lithium hydroxide monohydrate (0.27 g, 6.4 mmol) was added to an ice-cooled suspension of the methyl ester 269a) (1.0 g, 2.56 mmol) in THF/water (1:1, 50 mL) and the resulting mixture was stirred at room temperature for 16 h. The solvent was removed under vacuum, and the residue was dissolved in water (20 mL) and washed with dichloromethane (2×20 mL). The aqueous phase was acidified with sodium hydrogen sulfate and extracted with dichloromethane (3×50 mL). The combined organic layers were dried over sodium sulfate and evaporated to dryness. White solid. Yield: 0.9 g (93% of theory)
Workup
- temperaturecooled
- customThe solvent was removed under vacuum
- dissolutionthe residue was dissolved in water (20 mL)
- washwashed with dichloromethane (2×20 mL)
- extractionextracted with dichloromethane (3×50 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-0a09027d3aeb4f5b9b43f545df63364f
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315490B2
Reaction notes
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