Lithium hydroxide, monohydrate → 1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indole-6-carboxylic acid
Reaction equation
O.[OH-].[Li+].[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[N:13][C:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]([O:28]C)=[O:27])[CH:24]=3)[C:19]([S:30]([CH3:32])=[O:31])=[CH:18]2)=[N:15][CH:16]=1>O.C1COCC1.O>[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[N:13][C:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]([OH:28])=[O:27])[CH:24]=3)[C:19]([S:30]([CH3:32])=[O:31])=[CH:18]2)=[N:15][CH:16]=1Participants
5
Procedure
Lithium hydroxide monohydrate (0.34 g, 8.05 mmol) in water (2 mL) was added to an ice-cooled suspension of methyl ester 51d) (2.2 g, 5.37 mmol) in THF/water (1:1; 40 mL) and the resulting mixture was stirred at room temperature for 16 h. The solvent was removed under vacuum and the remnant was dissolved in water (20 mL) and washed with ethyl acetate (2×20 mL). The aqueous phase was acidified with sodium hydrogen sulfate and extracted with dichloromethane (2×50 mL). The organic layers were dried over sodium sulfate and evaporated. White solid. Yield: 1.8 g (85% of theory). HPLC-MS (method 5): Rt=2.6 min; m/z [M+H]+=396
Workup
- temperaturecooled
- customThe solvent was removed under vacuum
- dissolutionthe remnant was dissolved in water (20 mL)
- washwashed with ethyl acetate (2×20 mL)
- extractionextracted with dichloromethane (2×50 mL)
- dry with materialThe organic layers were dried over sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-fb25cdfebbae4ef3852b4a5fc4c95677
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315490B2
Reaction notes
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