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

HRID 1944390Notes

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

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of {5-fluoro-3-[3-(4-fluorobenzenesulfonyl)pyridin-4-ylmethyl]-2-methylindol-1-yl}acetic acid methyl ester (0.21 g) and tetrahydrofuran (1.0 mL) was treated with 5.0 M aqueous sodium hydroxide solution (3.0 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 to low bulk under reduced pressure. The resulting precipitate was collected by filtration, washed with water and dried to afford the title compound as a white solid (0.094 g).

Workup

concentrationconcentrated to low bulk under reduced pressure
filtrationThe resulting precipitate was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-5b9f3aa56e2c4ea6bfea9ae11f929d84
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394836B2

Reaction notes

Loading…