Stannane, tributyl(1-ethoxyethenyl)- → HCID 66634395, compound

HRID 1477761Notes

Reaction equation

HRID 1477761 reaction equation
[CH2:1]([O:3][C:4]([Sn](CCCC)(CCCC)CCCC)=[CH2:5])[CH3:2].Br[C:20]1[N:25]=[C:24]([O:26][CH3:27])[C:23]([N:28]2[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]2)=[CH:22][CH:21]=1>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:4]([O:3][C:1]([C:20]1[N:25]=[C:24]([O:26][CH3:27])[C:23]([N:28]2[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]2)=[CH:22][CH:21]=1)=[CH2:2])[CH3:5]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 576093006-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine

Product 1

HCID 66634395HCID 66634395, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1-Ethoxyvinyltri-n-butyltin (3.7 mL) was added to a suspension of 6-bromo-2-methoxy-3-(4-methyl-1H-imidazole-1-yl)pyridine (2.66 g) and bis(triphenylphosphine)palladium (II) chloride (350 mg) in dioxane (25 mL), and the mixture was stirred at 100° C. for five hours and 45 minutes. The reaction solution was left to cool to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography. The target fraction was concentrated. The resulting powder was triturated with diethyl ether-n-hexane and dried under reduced pressure to obtain 1.57 g of the title compound. Then, the mother liquor was concentrated to obtain 858 mg of the title compound. The property values of the compound are as follows: 1H-NMR (CDCl3) δ (ppm): 1.45 (t, J=7.2 Hz, 3H), 2.30 (s, 3H), 3.98 (q, J=7.2 Hz, 2H), 4.04 (s, 3H), 4.38 (d, J=1.6 Hz, 1H), 5.48 (d, J=1.6 Hz, 1H), 6.97 (s, 1H), 7.38 (d, j=8.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.78 (s, 1H).

Workup

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography
  5. concentrationThe target fraction was concentrated
  6. customThe resulting powder was triturated with diethyl ether-n-hexane
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-cbb19f01beff4c5cb182155fe0ec88df
Source dataset
uspto-grants-2016_08
Patent number
US09403815B2

Reaction notes

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