Sodium Hydroxide → 2-[5-Cyano-4-(trifluoromethyl)-1H-indol-1-yl]propanoic acid

HRID 1188568Notes

Reaction equation

[C:1]([C:3]1[C:4]([C:18]([F:21])([F:20])[F:19])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]([CH3:17])[C:13]([O:15]C)=[O:14])[CH:7]=[CH:6]2)#[N:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([C:3]1[C:4]([C:18]([F:21])([F:20])[F:19])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]([CH3:17])[C:13]([OH:15])=[O:14])[CH:7]=[CH:6]2)#[N:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To methyl 2-[5-cyano-4-(trifluoromethyl)-1H-indol-1-yl]propanoate (0.055 g, 0.185 mmol) in 1:1 THF/MeOH (4 mL) was added 5N NaOH (0.185 mL) and the resulting mixture was heated to 60° C. for 30 min. The cooled mixture was partitioned between Et2O and 0.1N HCl. The separated organic portion was washed with brine, dried over Na2SO4, and filtered. Concentration afforded the title compound (0.052 g, 99% yield): MS (APCI) m/z 283 (M+1).

Workup

customThe cooled mixture was partitioned between Et2O and 0.1N HCl
washThe separated organic portion was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationConcentration

Sources & evidence

ORD record: ord-e714abc0df3b41c2adcbbabb34d7cdcc
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673948B2

Reaction notes

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