Lithium hydroxide, monohydrate → 1-(5-(5-Ethyl-2-fluorophenyl)pyrimidin-2-yl)-3-(1-hydroxyethyl)-1H-indole-6-carboxylic acid

HRID 630542Notes

Reaction equation

HRID 630542 reaction equation
O.[OH-].[Li+].[CH2:4]([C:6]1[CH:7]=[CH:8][C:9]([F:34])=[C:10]([C:12]2[CH:13]=[N:14][C:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]([O:29]C)=[O:28])[CH:25]=4)[C:20]([CH:31]([OH:33])[CH3:32])=[CH:19]3)=[N:16][CH:17]=2)[CH:11]=1)[CH3:5]>C1COCC1.O>[CH2:4]([C:6]1[CH:7]=[CH:8][C:9]([F:34])=[C:10]([C:12]2[CH:17]=[N:16][C:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]([OH:29])=[O:28])[CH:25]=4)[C:20]([CH:31]([OH:33])[CH3:32])=[CH:19]3)=[N:14][CH:13]=2)[CH:11]=1)[CH3:5]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118676888Methyl 1-(5-(5-ethyl-2-fluorophenyl)pyrimidin-2-yl)-3-(1-hydroxyethyl)-1H-indole-6-carboxylate

Product 1

HCID 1186660901-(5-(5-Ethyl-2-fluorophenyl)pyrimidin-2-yl)-3-(1-hydroxyethyl)-1H-indole-6-carboxylic acid

Reagents, catalysts & solvents 1

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

Procedure

Lithium hydroxide monohydrate (33 mg, 0.786 mmol) was added to an ice-cooled suspension of 331d) (0.22 g, 0.524 mmol) in THF/water (1:1, 10 mL) and the resulting mixture was stirred at room temperature for 48 h. The THF was distilled off and the residue was diluted with water (5 mL) and acidified with saturated sodium hydrogen sulfate solution. A precipitating solid was filtered off and washed with water. Remaining humidity was removed by repeated azeotropic distillation of toluene. White solid. Yield: 0.17 g (80% of theory)

Workup

  1. temperaturecooled
  2. distillationThe THF was distilled off
  3. additionthe residue was diluted with water (5 mL)
  4. filtrationA precipitating solid was filtered off
  5. washwashed with water
  6. customwas removed
  7. distillationdistillation of toluene

Sources & evidence

ORD record
ord-8618bd73cfa9401a8078fa8ba7a99a75
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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