Thionyl Chloride → HCID 86638043, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16]([OH:18])=O)=[CH:10][CH:9]=1.S(Cl)([Cl:21])=O>>[ClH:21].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16]([Cl:21])=[O:18])=[CH:10][CH:9]=1Participants
Procedure
3-[6-(2-Fluoro-phenyl)-pyridin-3-yl]-acryloyl chloride hydrochloride salt was prepared in quantitative yield by boiling 3-[6-(2-fluoro-phenyl)-pyridin-3-yl]-acrylic acid in thionyl chloride, followed by removal of the volatiles by coevaporating three times with toluene. 3-[6-(2-Fluoro-phenyl)-pyridin-3-yl]-acryloyl chloride hydrochloride salt was dissolved in pyridine, and 1 equivalent of the respective amine was added. The reaction mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure, and residual pyridine was removed by coevaporating three times with toluene. The residue was dissolved in DMF, and the product was purified by preparative RP HPLC eluting with a gradient of 0 to 100% acetonitrile in water (+0.01% TFA). After lyophilization, the product was obtained as a solid.
Workup
- customfollowed by removal of the volatiles
- dissolution3-[6-(2-Fluoro-phenyl)-pyridin-3-yl]-acryloyl chloride hydrochloride salt was dissolved in pyridine
- customThe solvent was removed under reduced pressure, and residual pyridine
- customwas removed
- dissolutionThe residue was dissolved in DMF
- customthe product was purified by preparative RP HPLC
- washeluting with a gradient of 0 to 100% acetonitrile in water (+0.01% TFA)
- customAfter lyophilization, the product was obtained as a solid
Sources & evidence
- ORD record
- ord-fe8f6e5ea630437ba61e798ae0f93219
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304438B2
Reaction notes
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