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3-(Tributylstannyl)cyclohex-2-enone → HCID 57489644, Verbindung

HRID 2044095
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2044095
Cl[C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:30]1[CH2:35][CH2:34][CH2:33][C:32](=[O:36])[CH:31]=1)CCC>CN(C=O)C.C(Cl)Cl.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>[F:11][C:10]1[C:2]([C:30]2[CH2:35][CH2:34][CH2:33][C:32](=[O:36])[CH:31]=2)=[N:3][C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[C:5]([CH:9]=1)[C:6]([NH2:8])=[O:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 137768013-(Tributylstannyl)cyclohex-2-enoneHCID 574896456-Chloro-5-fluoro-2-(4-morpholinophenylamino)nicotinamide

Produkt 1

HCID 57489644HCID 57489644, VerbindungAusbeute 23,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysator
HCID 6228
Dimethylformamide
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 6-chloro-5-fluoro-2-(4-morpholinophenylamino)nicotinamide (80 mg, 0.228 mmol), 3-(tributylstannyl)cyclohex-2-enone (105 mg, 0.274 mmol) (synthesized according to literature procedure: Tet. Lett., 31:1837-1840 (1990)), and dichloro bis(triphenylphosphine)palladium (II) (16.05 mg, 0.023 mmol) in DMF (2 mL) was microwaved at 160° C. for 1 h. The reaction mixture was diluted with methylene chloride, washed with satd. NaHCO3, water, and concentrated. The residue was purified prep-HPLC. The product containing fractions were collected, basified with 1N NaOH, and extracted with methylene chloride twice. The combined organic fractions were washed with water, concentrated, and further purified by MPLC (ISCO, 5% ammonia/methanol/methylene chloride, 40 g silica gel column) to give 22 mg brown solid. LC-MS: (M+H)+=411.25. 1H NMR (500 MHz, DMSO-d6) δ ppm 10.76-10.84 (1H, m), 8.28-8.39 (1H, m), 8.13-8.21 (1H, m), 7.83-7.91 (1H, m), 7.45-7.53 (2H, m), 6.88-6.96 (2H, m), 6.52-6.57 (1H, m), 3.67-3.77 (4H, m), 3.04 (4H, d, J=4.95 Hz), 2.76-2.85 (2H, m), 2.39-2.46 (2H, m), 2.01-2.09 (2H, m).

Aufarbeitung

  1. washwashed with satd
  2. concentrationNaHCO3, water, and concentrated
  3. customThe residue was purified prep-HPLC
  4. additionThe product containing fractions
  5. customwere collected
  6. extractionextracted with methylene chloride twice
  7. washThe combined organic fractions were washed with water
  8. concentrationconcentrated
  9. customfurther purified by MPLC (ISCO, 5% ammonia/methanol/methylene chloride, 40 g silica gel column)

Quellen und Nachweise

ORD-Eintrag
ord-f15e82ba1ddc45239002fc49124fd2fb
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08586751B2

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