Cesium fluoride → HCID 59631216, compound

HRID 1431757Notes

Reaction equation

HRID 1431757 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:3]=1[CH3:19].[CH:20]([Sn](CCCC)(CCCC)CCCC)=[CH2:21].[F-].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[F:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([CH:20]=[CH2:21])=[C:3]([CH3:19])[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:5]2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 81998TributylvinyltinHCID 596310754-Chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

Product 1

HCID 59631216HCID 59631216, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (2.67 g, 9.79 mmol), bis(tri-tert-butylphosphine)palladium (0) (0.600 g, 1.175 mmol), vinyl tributyl tin (3.26 mL, 10.28 mmol), cesium fluoride (1.49 g, 9.79 mmol), and dioxane (20 mL) was stirred at 105° C. under nitrogen for 30 minutes, then concd. The resulting residue was partitioned between EtOAc and water, and the organic phase was dried over magnesium sulfate and concd. This afforded a crude material that was purified by column chromatography (silica; 0-60% EtOAc in hexanes) to yield 7-fluoro-3-methyl-2-(pyridin-2-yl)-4-vinylquinoline as a white amorphous solid. Mass Spectrum (ESI) m/e=265.2 (M+1).

Workup

  1. customThe resulting residue was partitioned between EtOAc and water
  2. dry with materialthe organic phase was dried over magnesium sulfate and concd
  3. customThis afforded a crude material that
  4. customwas purified by column chromatography (silica; 0-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d647089e890a4f7e8e6ee627e94243a3
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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