Sodium Hydroxide → 5-[4-(1-acetylpiperidin-4-yl)phenyl]-6-chloro-1H-indole-3-carboxylic acid

HRID 338377Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 5-[4-(1-acetylpiperidin-4-yl)phenyl]-6-chloro-1H-indole-3-carboxylate (120 mg, 0.30 mmol) in MeOH (4 mL) was added sodium hydroxide (1 mL, 1M). The mixture was heated to 70° C. for 24 h. Solvent was removed under reduced pressure. The residue was acidified to pH=5 and dried in vacuum to give an oil, which was purified by preparative HPLC to give the title compound (35 mg, 30% yield) as an off-white solid.

Workup

customSolvent was removed under reduced pressure
customdried in vacuum
customto give an oil, which
customwas purified by preparative HPLC

Sources & evidence

ORD record: ord-01bdba29354446eb9a05316cae9d326d
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889730B2

Reaction notes

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