Sodium Hydroxide → 3-(Indolin-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole

HRID 2402181Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]=[C:13]([C:15]4[S:16][C:17]([C:26]([F:29])([F:28])[F:27])=[C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:19]=4)[O:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]=[C:13]([C:15]4[S:16][C:17]([C:26]([F:27])([F:28])[F:29])=[C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:19]=4)[O:12][N:11]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 19 °C

Procedure

To a stirred solution of 3-(1H-indol-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole (40 mg, 0.097 mmol) in acetic acid at 12-14° C. was added slowly sodium cyanoborohydride (19 mg, 0.29 mmol). At the end of the addition the reaction was allowed to warm to 18-20° C. and was stirred for 2 h. After completion the reaction mixture was neutralized with 50% sodium hydroxide and extracted with ethyl acetate (50 ml×2). The organic layers were combined and dried over Na2SO4 and removed under reduced pressure. The crude indoline compound was purified by column chromatography using CH2Cl2/MeOH (9:1) to offer the product in 84.3% yield (33.8 mg, 0.082 mmol). MS (EI) m/z: 414 (M+)

Workup

additionAt the end of the addition the reaction
extractionextracted with ethyl acetate (50 ml×2)
dry with materialdried over Na2SO4
customremoved under reduced pressure
customThe crude indoline compound was purified by column chromatography

Sources & evidence

ORD record: ord-011e2316d4534eae83f7bd7b529920ff
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796318B2

Reaction notes

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