Hydrochloric Acid → {3-[2-(4-Chlorobenzenesulfonyl)pyridin-3-ylmethyl]-5-fluoro-2-methylindol-1-yl}acetic acid

HRID 1944387Notes

Reaction equation

C[O:2][C:3](=[O:33])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[C:17]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[N:18][CH:19]=[CH:20][CH:21]=2)=[C:6]1[CH3:32].[OH-].[Na+].Cl>O1CCCC1>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([S:22]([C:17]2[C:16]([CH2:15][C:7]3[C:8]4[C:13](=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=4)[N:5]([CH2:4][C:3]([OH:33])=[O:2])[C:6]=3[CH3:32])=[CH:21][CH:20]=[CH:19][N:18]=2)(=[O:24])=[O:23])=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of {3-[2-(4-chlorobenzenesulfonyl)pyridin-3-ylmethyl]-5-fluoro-2-methylindol-1-yl}acetic acid methyl ester (0.19 g) and tetrahydrofuran (1.5 mL) was treated with 5.0 M aqueous sodium hydroxide solution (2.0 mL), and the resulting mixture was stirred at 40° C. for 3 hours. The mixture was acidified by the addition of 5.0 M aqueous hydrochloric acid solution and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (3.5:6.5 to 9:1 by volume) to afford the title compound as a white solid (0.039 g).

Workup

concentrationconcentrated under reduced pressure
customThe residue was purified by preparative reverse-phase HPLC
washeluting with a mixture of acetonitrile and water (3.5:6.5 to 9:1 by volume)

Sources & evidence

ORD record: ord-3576c6a0eadd433cbd52fd257a21d00f
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394836B2

Reaction notes

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