Dimethylformamide → N-[3-(5-{2-[3-pyridyl]ethenyl}fur-2-yl)-1-methyl-2-propynyl]-N-hydroxyurea

HRID 52171

Reaktionsgleichung

Reaktionsgleichung von HRID 52171
I[C:2]1[O:3][C:4]([CH:7]=[CH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:6]=1.[OH:15][N:16]([CH:20]([C:22]#[CH:23])[CH3:21])[C:17]([NH2:19])=[O:18].CN(C)C=O.[NH4+].[OH-]>C(NCC)C.CC#N.CC#N.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([CH:8]=[CH:7][C:4]2[O:3][C:2]([C:23]#[C:22][CH:20]([N:16]([OH:15])[C:17]([NH2:19])=[O:18])[CH3:21])=[CH:6][CH:5]=2)[CH:10]=1

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 19963264N-hydroxy-N-(butyn-2-yl)ureaHCID 545240982-Iodo-5-[2-{3-pyridyl}ethenyl]furan

Produkt 1

HCID 53636693N-[3-(5-{2-[3-pyridyl]ethenyl}fur-2-yl)-1-methyl-2-propynyl]-N-hydroxyureaAusbeute 37,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysatorHCID 6093782Bis(acetonitrile)dichloropalladiumKatalysatorHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-iodo-5-[2-{3-pyridyl}ethenyl]furan (1.4 g, 4.7 mmol), prepared as in step 5, and N-hydroxy-N-(butyn-2-yl)urea (0.64 g, 5 mmol), prepared as in step 2, in diethylamine (10 mL) was added dimethylformamide (1 mL), triphenylphosphine (0.026 g, 0.1 mmol), cuprous iodide (5 mg, 25 mmol) and bis(acetonitrile)palladium(II) chloride (13 mg, 50 mmol). The mixture was stirred overnight at ambient temperature. Aqueous NH4OH was added and the mixture extracted thoroughly with CH2Cl2. The combined organic layer was washed with brine, dried (MgSO4) and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel eluting with 5% MeOH--CH2Cl2 to afford an off-white solid. Recrystallization from ethyl acetate-hexanes gave 530 mg of the title compound. m.p. 166° C. 1H NMR (DMSO-d6, 300 MHz) δ1.38 (d, J=7 Hz, 3H), 5.19 (q, J=7 Hz, 1H), 6.61 (bs, 2H), 6.82 (d, J=3 Hz, 1H), 6.82 (d, J=3 Hz, 1H), 7.09 (d, J=16 Hz, 1H), 7.25 (d, J=16 Hz, 1H), 7.39 (m, 1H), 7.77 (m, 1H), 8.03 (m, 1H), 8.45 (m, 1H), 8.77 (m, 1H), 9.43 (s, 1H). MS (DCI/NH3) m/e 298 (M+H)+. Anal calcd for C16H15N3O3 : C, 64.63; H, 5.08; N, 14.13. Found: C, 64.01; H, 5.09; N, 14.06.

Aufarbeitung

  1. extractionthe mixture extracted thoroughly with CH2Cl2
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel eluting with 5% MeOH
  6. customCH2Cl2 to afford an off-white solid
  7. customRecrystallization from ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4b0f31714e074fc6b058cad5f5fa22a2
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616596

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