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

HRID 338339Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of compound methyl 6-chloro-5-{4-[2-(piperazin-1-yl)ethoxy]phenyl}-1H-indole-3-carboxylate (80 mg, 0.22 mmol) in methanol (8 mL) was added aq. NaOH (2 mL, 1.0 N). 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 (10 mg, 11% yield) as a white solid. MS (ES+) 400.2 (M+H)+. 1H NMR (400 MHz, DMSO-d6): δ 12.00 (s, 1H), 8.35 (s, 1H), 8.05 (s, 1H), 7.95 (s, 1H), 7.60 (s, 1H), 7.35 (d, 2H), 7.00 (m, 2H), 4.10 (m, 2H), 2.90 (m, 4H), 2.70 (m, 2H), 2.60 (m, 4H).

Workup

custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-ca1d56d967b6424d888686cd7ea8c5e1
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889730B2

Reaction notes

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