Nitrogen → 2-Vinylquinoline

HRID 1777772Notes

Reaction equation

HRID 1777772 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.N#N.[CH2:14]([Sn](CCCC)(CCCC)C=C)[CH2:15]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:14]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)=[CH2:15]

Participants

6

Reactant 3

HCID 947NitrogenHCID 119282-ChloroquinolineHCID 81998Tributylvinyltin

Product 1

HCID 698752-VinylquinolineYield 74%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

2-chloroquinoline (1-1) (1.00 g, 6.1 mmol) in toluene (25 mL) was sparged with N2 gas for 5 min, and tributyl(vinyl)stannane (2.52 g, 2.33 mL, 8.0 mmol) and tetrakis(triphenylphosphine)palladium (0.353 g, 0.31 mmol) were added. The mixture was heated at 125° C. for 1 h, then cooled and concentrated in vacuo. The residue was suspended in CH2Cl2 (20 mL) and purified by silica gel flash column chromatography (80 g cartridge), eluting with 0-30% EtOAc/hexanes over 20 min. The fractions containing the desired product (1-2) were pooled, and after solvent removal in vacuo, 700 mg (74%) of a clear oil were obtained. LC/MS: m/z (M+H)=156.0.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel flash column chromatography (80 g cartridge)
  4. washeluting with 0-30% EtOAc/hexanes over 20 min
  5. additionThe fractions containing the desired product (1-2)
  6. customafter solvent removal in vacuo

Sources & evidence

ORD record
ord-68405c5b8e2a4077aad06b93ab2767d7
Source dataset
uspto-grants-2016_02
Patent number
US09266881B2

Reaction notes

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