Stannane, tributyl(1-ethoxyethenyl)- → 1-(3-(1-(Quinolin-6-yl)cyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

HRID 456116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456116
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3([C:14]4[CH:15]=[C:16]5[C:21](=[CH:22][CH:23]=4)[N:20]=[CH:19][CH:18]=[CH:17]5)[CH2:13][CH2:12]3)=[N:9][N:10]=2)[N:7]=1.C([Sn](CCCC)(CCCC)[C:29]([O:31]CC)=[CH2:30])CCC>O1CCOCC1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:20]1[C:21]2[C:16](=[CH:15][C:14]([C:11]3([C:8]4[N:6]5[N:7]=[C:2]([C:29](=[O:31])[CH3:30])[CH:3]=[CH:4][C:5]5=[N:10][N:9]=4)[CH2:13][CH2:12]3)=[CH:23][CH:22]=2)[CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 581905686-(1-(6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)cyclopropyl)quinoline

Produkt 1

HCID 581905101-(3-(1-(Quinolin-6-yl)cyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 6-[1-(6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)-cyclopropyl]-quinoline (30 mg, 0.093 mmol), PdCl2(PPh3)2 (6.5 mg, 0.0093 mmol) and tributyl(1-ethoxyvinyl)stannane (67 mg, 0.186 mmol) in 1,4-dioxane (3 mL) was heated at 90° C. for 3 h under N2. The reaction mixture was diluted with EtOAc, washed with aqueous KF. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in HOAc and 3 N HCl, and stirred at room temperature for 3 h. The solvent was removed in vacuo and the residue was dissolved in DCM, washed with sat. aq. NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography in silica gel eluting with a EtOAC/MeOH gradient to afford the title compound as yellow solid. 1H-NMR (400 MHz, CDCl3) δ ppm 8.89 (dd, 1H); 8.13-8.04 (m, 3H), 7.93 (d, 1H), 7.87 (dd, 1H), 7.70 (d, 1H), 7.40 (dd, 1H), 2.51 (s, 3H), 1.92-1.89 (m, 2H), 1.73-1.69 (m, 2H). LCMS (method A): [MH]+=330, tR=4.18 min.

Aufarbeitung

  1. washwashed with aqueous KF
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in HOAc
  6. customThe solvent was removed in vacuo
  7. dissolutionthe residue was dissolved in DCM
  8. washwashed with sat. aq. NaHCO3 and brine
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash chromatography in silica gel eluting with a EtOAC/MeOH gradient

Quellen und Nachweise

ORD-Eintrag
ord-257e5fad7f7744e0b99e27db70022978
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497368B2

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