Tributylvinyltin → Methyl 4-methyl-6-(3-methyl-1-tosyl-1H-indol-4-yl)-2-vinylnicotinate

HRID 80820Notes

Reaction equation

HRID 80820 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[C:14]([CH3:31])=[CH:15][N:16]3[S:21]([C:24]2[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH:9]=[C:8]([CH3:32])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:33]([Sn](CCCC)(CCCC)C=C)[CH2:34]CC>CN(C=O)C>[CH3:32][C:8]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([CH:33]=[CH2:34])[N:11]=[C:10]([C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[C:14]([CH3:31])=[CH:15][N:16]3[S:21]([C:24]2[CH:25]=[CH:26][C:27]([CH3:28])=[CH:29][CH:30]=2)(=[O:22])=[O:23])[CH:9]=1

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 86690266Methyl 2-chloro-4-methyl-6-(3-methyl-1-tosyl-1H-indol-4-yl)nicotinate

Product 1

HCID 86690267Methyl 4-methyl-6-(3-methyl-1-tosyl-1H-indol-4-yl)-2-vinylnicotinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of methyl 2-chloro-4-methyl-6-(3-methyl-1-tosyl-1H-indol-4-yl)nicotinate (0.348 g, 0.742 mmol) in DMF (5 mL) was sparged with argon for 10 min before trans-Pd(PPh3)2Cl2 (0.052 g, 0.074 mmol), tri-n-butyl(vinyl)tin (0.353 g, 1.11 mmol), and BHT (0.016 g, 0.074 mmol) were added. The resulting suspension was sparged with argon for 5 min and the vessel was sealed and heated at 60° C. After 24 h the reaction was allowed to cool to rt and 50% KF on Celite® was added. The resulting slurry was then filtered over Celite® eluting with EtOAc. The organic was then washed with 10% KF in water and then dried (Na2SO4), filtered and concentrated. The residue was then purified by FCC (5-40% EtOAc/heptane) to give the title compound. MS ESI m/z 461.1 (M+H)+.

Workup

  1. additionwere added
  2. customThe resulting suspension was sparged with argon for 5 min
  3. customthe vessel was sealed
  4. temperatureto cool to rt
  5. addition50% KF on Celite® was added
  6. filtrationThe resulting slurry was then filtered over Celite®
  7. washeluting with EtOAc
  8. washThe organic was then washed with 10% KF in water
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was then purified by FCC (5-40% EtOAc/heptane)

Sources & evidence

ORD record
ord-70114c280f9a4103a5aae60ef39c4175
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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