Sodium Hydroxide → 6-chloro-5-(4-{[(1S,2S)-2-hydroxycyclohexyl]oxy}phenyl)-1H-indole-3-carboxylic acid

HRID 338341Notes

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][C@H:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]2[OH:28])=[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][C@H:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]2[OH:28])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 6-chloro-5-(4-{[(1S,2S)-2-hydroxycyclohexyl]oxy}phenyl)-1H-indole-3-carboxylate (80 mg, 0.22 mmol) in methanol (8 mL) was added aq. 1.0M 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 (12.6 mg, 16% yield) as a white solid. MS (ES+) 408.2 (M+Na)+. 1H NMR (400 MHz, DMSO-d6): δ 12.40-11.90 (br. s, 1H), 11.85 (s, 1H), 8.10 (s, 1H), 7.90 (s, 1H), 7.61 (m, 1H), 7.32 (d, 2H), 7.00 (d, 2H), 4.93 (m, 1H), 4.10 (m, 1H), 3.57 (m, 1H), 2.05 (m, 1H), 1.88 (m, 1H), 1.53 (m, 2H), 1.40-1.10 (m, 4H).

Workup

custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-3c11cd71e0854bb985f5363aae2e3be2
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889730B2

Reaction notes

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