Hydrochloric Acid → HCID 66657860, compound

HRID 420976Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH:37]([CH3:39])[CH3:38])=[CH:32][CH:31]=2)[C:8]2[C:13]([C:14]=1[C:15]([O:17]CC)=[O:16])=[CH:12][C:11]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1)=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[CH:37]([O:36][C:33]1[CH:34]=[CH:35][C:30]([N:7]2[C:8]3[C:13](=[CH:12][C:11]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:22][N:21]=4)=[CH:10][CH:9]=3)[C:14]([C:15]([OH:17])=[O:16])=[C:6]2[C:4]([OH:5])=[O:3])=[CH:31][CH:32]=1)([CH3:39])[CH3:38]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-(4-isopropoxyphenyl)-5-(5-trifluoromethylpyridin-2-yl)indole-2,3-dicarboxylic acid diethyl ester hydrochloric salt (150 mg, 0.26 mmol, see step (d) above), NaOH (aq, 2 M, 2 mL) and dioxane (3) mL) was heated at 80° C. for 4 h. After cooling, the reaction mixture was acidified with HCl (aq, IM) to pH 5 and filtered. The solid was recrystallised from EtOAc/petroleum ether to afford the title compound. Yield 96 mg (76%).

Workup

temperatureAfter cooling
filtrationfiltered
customThe solid was recrystallised from EtOAc/petroleum ether

Sources & evidence

ORD record: ord-09281b42a01b4ab6af955b25a3cc3a1b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097623B2

Reaction notes

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