2-Propanethiol → 3-(2-Isopropylthio-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

Reaction equation

Cl[C:2]1[C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1.[CH3:17][CH:18]([SH:20])[CH3:19].[H-].[Na+]>>[CH:18]([S:20][C:2]1[C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1)([CH3:19])[CH3:17]

Participants

Reactant 3

HCID 63642-Propanethiol

HCID 24758Sodium hydride

HCID 723356323-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

Product 1

HCID 687816783-(2-Isopropylthio-6-trifluoromethyl-pyridin-3-yl)-acrylic acidYield 36.3%

Procedure

3-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (245 mg, 0.974 mmol) was reacted with 2-propanthiol (240 mg, 3.15 mmol) and sodium hydride (143 mg, 3.56 mmol) to afford the title compound (103 mg) after purification by column chromatography (Hex/EtOAc=2.5/1).

Sources & evidence

ORD record: ord-2e6d13fe45764c3b919ebb84e24e2033
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858621B2

Reaction notes

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