Sodium Hydroxide → HCID 86698689, compound

HRID 338343Notes

Reaction equation

HRID 338343 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]([CH3:21])=[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:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86698688HCID 86698688, compound

Product 1

HCID 86698689HCID 86698689, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 6-chloro-5-(4-methylphenyl)-1H-indole-3-carboxylate (80 mg, 0.22 mmol) in methanol (8 mL) was added 1.0M aqueous 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 (10 mg, 13% yield) as a white solid. MS (ES+) 286.1 (M+H)+. 1H NMR (400 MHz, DMSO): δ 12.20-11.95 (br. s, 1H), 11.90 (br. s, H), 8.10 (s, 1H), 7.95 (s, 1H), 7.65 (s, 1H), 7.35-7.20 (m, 4H), 2.35 (s, 3H).

Workup

  1. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-2e3cf9c4260c4a08939096b949765b0f
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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