Sodium Hydroxide → 2-(6-(7-Methyl-1-oxoisoindolin-2-yl)-1H-indol-1-yl)acetic acid

HRID 453864Notes

Reaction equation

[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[C:11](=[O:13])[N:10]([C:14]1[CH:22]=[C:21]3[C:17]([CH:18]=[CH:19][N:20]3[CH2:23][C:24]([O:26]CC)=[O:25])=[CH:16][CH:15]=1)[CH2:9]2>O.C1COCC1.CO>[CH3:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[C:11](=[O:13])[N:10]([C:14]1[CH:22]=[C:21]3[C:17]([CH:18]=[CH:19][N:20]3[CH2:23][C:24]([OH:26])=[O:25])=[CH:16][CH:15]=1)[CH2:9]2

Participants

Conditions

Temperature: 25 °C

Procedure

NaOH (1.86 mmol, 1.3 equiv.), dissolved in water (6 ml), was added to a solution of ethyl 2-(6-(7-methyl-1-oxoisoindolin-2-yl)-1H-indol-1-yl)acetate (1.44 mmol, 1 equiv.) in THF/MeOH (1:1, 5 ml), and the mixture was stirred for 2 h at 25° C. The reaction solution was concentrated under reduced pressure, and the aqueous residue was adjusted to pH 3 with 1 M HCl and extracted with ethyl acetate (3×50 ml). The combined organic phases were dried over Na2SO4 and concentrated under reduced pressure. Yield: quantitative

Workup

concentrationThe reaction solution was concentrated under reduced pressure
extractionextracted with ethyl acetate (3×50 ml)
dry with materialThe combined organic phases were dried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3dadbd3fa1dc4eb9ba6bde14b16b80b9
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492559B2

Reaction notes

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