Lithium hydroxide, monohydrate → 1-(5-Bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acid

HRID 630499Notes

Reaction equation

HRID 630499 reaction equation
O.[OH-].[Li+].[Br:4][C:5]1[CH:6]=[N:7][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22]C)=[O:21])[CH:18]=3)[C:13]([S:24][CH3:25])=[CH:12]2)=[N:9][CH:10]=1>C1COCC1.O>[Br:4][C:5]1[CH:6]=[N:7][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:22])=[O:21])[CH:18]=3)[C:13]([S:24][CH3:25])=[CH:12]2)=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118666039Methyl 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate

Product 1

HCID 1186660601-(5-Bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acid

Reagents, catalysts & solvents 1

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

Procedure

Lithium hydroxide monohydrate (1.63 g, 39.78 mmol) was added to an ice-cooled suspension of 51b) (5 g, 13.26 mmol) in THF/water (1:1, 50 mL) and the resulting mixture was stirred at room temperature for 16 h. The solvents were removed under reduced pressure and the residue was dissolved in water (20 mL). The aqueous solution was washed with ethyl acetate (2×20 mL), acidified with sodium hydrogen sulfate and extracted with dichloromethane (3×50 mL). The combined organic layers were dried over sodium sulfate and evaporated. White solid. Yield: 4 g (83% of theory)

Workup

  1. temperaturecooled
  2. customThe solvents were removed under reduced pressure
  3. dissolutionthe residue was dissolved in water (20 mL)
  4. washThe aqueous solution was washed with ethyl acetate (2×20 mL)
  5. extractionextracted with dichloromethane (3×50 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-00bf6cabb12b44f9b28864283d555c71
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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