Tributylvinyltin → HCID 86732058, compound

HRID 1498795Notes

Reaction equation

HRID 1498795 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[C:13]([CH3:14])=[N:12][C:11]([CH3:15])=[N:10]2)[CH:3]=1.[CH2:16]([Sn](CCCC)(CCCC)C=C)[CH2:17]CC>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][C:11]1[N:12]=[C:13]([CH3:14])[N:9]([C:4]2[CH:3]=[C:2]([CH:16]=[CH2:17])[CH:7]=[C:6]([CH3:8])[N:5]=2)[N:10]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 86732059HCID 86732059, compound

Product 1

HCID 86732058HCID 86732058, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methylpyridine (24-3, 456 mg, 2.05 mmol), tributyl(vinyl)tin (845 mg, 2.67 mmol), and tetrakis(triphenylphosphine)-palladium(0) (118 mg, 0.102 mmol) in toluene (10 mL) was refluxed under an atmosphere of argon for 2 hours and cooled to room temperature. The mixture was concentrated and the residue was purified by silica gel column chromatography (0-90% ethyl acetate in hexanes) to give 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methyl-4-vinylpyridine (25-1) as a light yellow oil. 1H NMR (300 MHz, CDCl3) 57.60 (s, 1H), 7.09 (s, 1H), 6.68 (dd, 1H, J=17.6, 10.9 Hz), 6.03 (d, 1H, J=17.6 Hz), 5.52 (d, 1H, J=10.9 Hz), 2.81 (s, 3H), 2.55 (s, 3H), 2.42 (s, 3H). LRMS m/z (M+H) 215 found, 215 required.

Workup

  1. temperaturewas refluxed under an atmosphere of argon for 2 hours
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (0-90% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9a412651afbf49a1ba2d13dfca4a1c5e
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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