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Lithium hydroxide, monohydrate → 1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indole-6-carboxylic acid

HRID 630468
Notes
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Reaction equation

HRID 630468 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118666349Methyl 1-(5-(2-fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indole-6-carboxylate

Product 1

HCID 1186660891-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indole-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883
Oxolane--water (1/1)
Solvent

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

  1. temperaturecooled
  2. customThe solvent was removed under vacuum
  3. dissolutionthe remnant was dissolved in water (20 mL)
  4. washwashed with ethyl acetate (2×20 mL)
  5. extractionextracted with dichloromethane (2×50 mL)
  6. dry with materialThe organic layers were dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-fb25cdfebbae4ef3852b4a5fc4c95677
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09315490B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes