Sodium Acetate → 5-(3,5-Dimethylisoxazol-4-yl)-2-oxo-3-phenylindolin-3-yl acetate

HRID 1052959Notes

Reaction equation

Cl[C:2]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:12]([CH3:17])=[N:13][O:14][C:15]=3[CH3:16])[CH:9]=2)[NH:4][C:3]1=[O:18].[C:25]([O-:28])(=[O:27])[CH3:26].[Na+]>O1CCOCC1>[C:25]([O:28][C:2]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:12]([CH3:17])=[N:13][O:14][C:15]=3[CH3:16])[CH:9]=2)[NH:4][C:3]1=[O:18])(=[O:27])[CH3:26]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 3-chloro-5-(3,5-dimethylisoxazol-4-yl)-3-phenylindolin-2-one (50 mg, 0.15 mmol) in dioxane (2 mL) was added sodium acetate (90 mg, 1.1 mmol), the reaction mixture was stirred at 85° C. for 6 h and quenched by the addition of saturated ammonium chloride solution (10 mL). The organic layer was extracted with CH2Cl2 (2×20 mL). The combined organic layers was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford crude product, ant it was purified by Pre-TLC (eluent: Hexane/EtOAc=1/1) to give product (20 mg, 37%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.78 (s, 1H), 7.33-7.38 (m, 6H), 7.25 (s, 1H), 7.01 (d, J=8.0 Hz, 1H), 2.35 (s, 3H), 2.18 (s, 3H), 2.15 (s, 3H). MS (ESI) m/e [M+1]+ 363.

Workup

customquenched by the addition of saturated ammonium chloride solution (10 mL)
extractionThe organic layer was extracted with CH2Cl2 (2×20 mL)
dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customto afford crude product, ant it
customwas purified by Pre-TLC (eluent: Hexane/EtOAc=1/1)

Sources & evidence

ORD record: ord-748f824edaa144c6a59247547298e425
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09393232B2

Reaction notes

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