Sodium Hydroxide → [6-Chloro-1-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

HRID 1631496Notes

Reaction equation

HRID 1631496 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:33])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][C:12]([Cl:16])=[CH:13][CH:14]=2)[N:9]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][C:19]=2[C:28]([F:31])([F:30])[F:29])[C:8]=1[CH3:32]>C1COCC1.CO>[Cl:16][C:12]1[N:11]=[C:10]2[N:9]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][C:19]=3[C:28]([F:29])([F:31])[F:30])[C:8]([CH3:32])=[C:7]([CH2:6][C:5]([OH:33])=[O:4])[C:15]2=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86620148[6-Chloro-1-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester

Product 1

HCID 11641177[6-Chloro-1-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1M Aqueous NaOH (0.25 ml) is added to a stirring suspension of [6-chloro-1-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester: (0.01 g, 0.021 mmol) in 1:1 THF/MeOH (0.5 ml). The resulting suspension is sonicated and allowed to stir at room temperature overnight. The solvent is removed in vacuo and the crude solid is dissolved in water (0.5 ml) and acidified to pH 2-3 using 1 N HCl. The suspension which forms is filtered, washed with water (0.5 ml) and dried under high vacuum to yield the titled compound. (MH+ 461)

Workup

  1. customThe resulting suspension is sonicated
  2. customThe solvent is removed in vacuo
  3. dissolutionthe crude solid is dissolved in water (0.5 ml)
  4. filtrationThe suspension which forms is filtered
  5. washwashed with water (0.5 ml)
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-6b585b655ca24eac841b26f6b868e3ac
Source dataset
uspto-grants-2014_07
Patent number
US08791256B2

Reaction notes

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