Potassium Hydroxide → [3-(2-Benzenesulfonylpyridin-3-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid

HRID 41867Notes

Reaction equation

HRID 41867 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]([CH2:16][C:17]2[C:18]([S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])=[N:19][CH:20]=[CH:21][CH:22]=2)=[C:7]1[CH3:32])C.[OH-].[K+]>C1COCC1.O>[C:26]1([S:23]([C:18]2[C:17]([CH2:16][C:8]3[C:9]4[C:14](=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=4)[N:6]([CH2:5][C:4]([OH:33])=[O:3])[C:7]=3[CH3:32])=[CH:22][CH:21]=[CH:20][N:19]=2)(=[O:25])=[O:24])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59380589[3-(2-Benzenesulfonyl-pyridin-3-ylmethyl)-5-fluoro-2-methyl-indol-1-yl]-acetic acid ethyl ester

Product 1

HCID 59380586[3-(2-Benzenesulfonylpyridin-3-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acidYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [3-(2-benzenesulfonyl-pyridin-3-ylmethyl)-5-fluoro-2-methyl-indol-1-yl]-acetic acid ethyl ester (1.20 g, 2.56 mmol) in THF (26 ml) was added a solution of potassium hydroxide (0.43 g, 7.68 mmol) in water (9 ml). The resulting solution was stirred at room temperature for 3.5 h. THF was removed in vacuo and the remaining aqueous layer was acidified with aqueous HCl (0.1 M, 25 ml). The product was collected by filtration, washed with water and dried in vacuo to afford 1.12 g (100%) of the title compound (LCMS RT=4.58 min, M+-H 437.2).

Workup

  1. customTHF was removed in vacuo
  2. filtrationThe product was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1055bdbd06164a2ab822933771e1968b
Source dataset
uspto-grants-2013_09
Patent number
US08536158B2

Reaction notes

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