Hydrochloric Acid → 1-(3,5-Difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indole-6-carboxylic acid

HRID 1645178Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N+:30]([O-:32])=[O:31])=[CH:10][N:11]2[CH2:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=2)=[CH:7][CH:6]=1)=[O:4].O[Li].O.Cl>O1CCOCC1.O>[F:22][C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([F:21])[CH:18]=1)[CH2:14][N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:13]=2)[C:9]([S:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N+:30]([O-:32])=[O:31])=[CH:10]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(3,5-Difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indole-6-carboxylic acid methyl ester (150.0 mg, 0.33 mmol) in dioxane (20 mL) and water (15 mL) was added LiOH.H2O (83.1 mg, 2.0 mmol) in 5 ml water. The reaction mixture was stirred overnight at 60° C. The mixture was then acidified to pH 4 by addition of 15% aqueous HCl and the mixture was extracted twice with ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give a yellow powder. The product was recrystallised from heptane/ethyl acetate to give the title compound as yellow/orange crystals (129.3 mg, y=89%)

Workup

extractionthe mixture was extracted twice with ethyl acetate
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated in vacuo
customto give a yellow powder
customThe product was recrystallised from heptane/ethyl acetate

Sources & evidence

ORD record: ord-e94bc8cbf58e495286380af33bd7ac32
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124647B2

Reaction notes

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