Triethylamine → Methyl 3-ethenylpyridine-2-carboxylate
Reaction equation
Br[C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:12]([B-](F)(F)F)=[CH2:13].[K+].C(N(CC)CC)C>CC(O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:12]([C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)=[CH2:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
Methyl 3-bromopyridine-2-carboxylate (1.0 g, 4.63 mmol) and potassium vinyltrifluoroborate (CAS number 13682-77-4; 0.744 g, 5.56 mmol) were dissolved in IPA (15 ml). To this was then added triethylamine (0.467 g, 4.63 mmol) and the mixture was degassed under nitrogen atmosphere for 15 minutes. [1,1′-Bis(diphenyl phosphino)ferrocene]dichloropalladium(II) (0.075 g, 0.092 mmol) was added and the reaction was stirred at 100° C. for 4 hours. The reaction was diluted with water (75 ml) and filtered through diatomaceous earth (commercially sold under the trade mark “Celite”). The organics were extracted with ethyl acetate (3×50 ml), washed with water (25 ml), brine (20 ml), dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-18% ethyl acetate/n-hexane to afford the title compound.
Workup
- filtrationfiltered through diatomaceous earth (
- extractionThe organics were extracted with ethyl acetate (3×50 ml)
- washwashed with water (25 ml), brine (20 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by column chromatography (silica, 0-18% ethyl acetate/n-hexane
Sources & evidence
- ORD record
- ord-5f023345960c4a92b4a016f757b09621
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156829B2
Reaction notes
Loading…