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

HRID 924978Notes

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-400e6c3acb6143ab8e5e5e27b93a1ccc
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09283229B2

Reaction notes

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