Tributylvinyltin → 5-Bromo-2,7-dimethyl-6-vinylquinoline

HRID 931729Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:8]([Br:19])=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:17])[N:13]=[C:12]([CH3:18])[CH:11]=[CH:10]2)(=O)=O.[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC.[Cl-].[Li+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:19][C:8]1[C:7]([CH:22]=[CH2:23])=[C:16]([CH3:17])[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12]([CH3:18])=[N:13]2

Participants

Conditions

Temperature: 80 °C

Procedure

PdCl2(PPh3)2 (207 mg, 0.30 mmol) was added to a mixture of 5-bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate (5A) (1.13 g, 2.95 mmol), tributyl(vinyl)stannane (0.95 mL, 3.25 mmol) and lithium chloride (375 mg, 8.85 mmol) in DMF (30 mL). The reaction mixture was flushed with argon, heated at 80° C. for 4 hours, and then the volatile component was removed in vacuo. The residue was dissolved in ethyl acetate (200 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide 5B (678 mg, 88%). LCMS-ESI+ (m/z): 262.1, 264.1 (M+H)+.

Workup

customThe reaction mixture was flushed with argon
customthe volatile component was removed in vacuo
dissolutionThe residue was dissolved in ethyl acetate (200 mL)
washwashed with NaHCO3 solution, water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record: ord-f9dbf59a0b9c4a1bbadeae227350fe9d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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