Ethyl 3-oxo-3-(pyridin-3-yl)-2-(thiophen-3-yl)propanoate → 1-(Pyridin-3-yl)-2-(thiophen-3-yl)ethanone

HRID 401188Notes

Reaction equation

[O:1]=[C:2]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH:3]([C:9]1[CH:13]=[CH:12][S:11][CH:10]=1)C(OCC)=O>CS(C)=O.[Cl-].[Na+].O.O>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:2](=[O:1])[CH2:3][C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH:15]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of ethyl 3-oxo-3-(pyridin-3-yl)-2-(thiophen-3-yl)propanoate (2 g, 7.26 mmol) in DMSO (20 mL) was added catalytic amount of brine (0.2 mL). The reaction mixture was heated at 160° C. for 2 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc. The organic layer was concentrated in vacuo and purified by column chromatography to afford Intermediate 56 (1 g, yield 68%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with EtOAc
concentrationThe organic layer was concentrated in vacuo
custompurified by column chromatography

Sources & evidence

ORD record: ord-2660691955f94b00afea2e841526eb28
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741915B2

Reaction notes

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