Sodium Hydroxide → 5-[4-(1-acetylazetidin-2-yl)phenyl]-6-chloro-1H-indole-3-carboxylic acid

HRID 1054678Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 5-[4-(1-acetylazetidin-2-yl)phenyl]-6-chloro-1H-indole-3-carboxylate (40 mg, 0.11 mmol) in methanol (8 mL) was added 1.0 M aq. NaOH (2.0 mL, 2.0 mmol). The mixture was stirred at 70° C. for 24 hours. The mixture was adjusted to pH 7 and purified by reverse phase HPLC to give the title compound (3 mg, 7% yield) as a white solid.

Workup

custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-68d6f98c47c34d0da62db6aa9faf1ec4
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394285B2

Reaction notes

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