Tributylvinyltin → 2-Ethenyl-1,5-naphthyridine

HRID 1777788Notes

Reaction equation

HRID 1777788 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[N:3]=1.[CH2:12]([Sn](CCCC)(CCCC)C=C)[CH2:13]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:12]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[N:3]=1)=[CH2:13]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 151530312-Chloro-1,5-naphthyridine

Product 1

HCID 571924222-Ethenyl-1,5-naphthyridineYield 57.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

2-chloro-1,5-naphthyridine (10-1) (35 g, 213 mmol) in toluene (420 mL) was treated with tributyl(vinyl)stannane (101 g, 93.4 mL, 319 mmol) and tetrakis(triphenylphosphine)palladium (36.9 g, 31.9 mmol). The mixture was heated at 140° C. under microwave irradiation for 20 min, then cooled and concentrated in vacuo. The residue was purified by silica gel flash column chromatography, eluting with 0-100% EtOAc/heptane. The fractions containing the desired product (10-2) were pooled, and after solvent removal in vacuo, 19 g (57%) of the product were obtained. LC/MS: m/z (M+H)=157.2.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel flash column chromatography
  4. washeluting with 0-100% EtOAc/heptane
  5. additionThe fractions containing the desired product (10-2)
  6. customafter solvent removal in vacuo

Sources & evidence

ORD record
ord-df60676b5ae447b7ada47f9f5a7becf2
Source dataset
uspto-grants-2016_02
Patent number
US09266881B2

Reaction notes

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