Cesium carbonate → HCID 56953296, Verbindung

HRID 2366201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366201
Br[C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[CH:19]1([NH:22][C:23]([NH2:25])=[O:24])[CH2:21][CH2:20]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([F:17])[C:11]=1[C:9]1[S:8][C:7]2[C:2]([NH:25][C:23]([NH:22][CH:19]3[CH2:21][CH2:20]3)=[O:24])=[N:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 2726261-CyclopropylureaHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866689904-Bromo-2-(2-chloro-6-fluorophenyl)thiazolo[5,4-c]pyridine

Produkt 1

HCID 56953296HCID 56953296, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a microwave tube was added 4-bromo-2-(2-chloro-6-fluorophenyl)thiazolo[5,4-c]pyridine (0.050 g, 1.5 mmol), 1-cyclopropylurea (0.043 g, 0.22 mmol), Pd2(dba)3 (0.013 g, 0.017 mmol), XantPhos (0.017 g, 0.034 mmol) and Cs2CO3 (0.11 g, 0.34 mmol) in dioxane (2.0 mL). The mixture was degassed with N2 for 10 minutes and then irradiated in a microwave reactor at 160° C. for 2 hours. After cooling to room temperature, solid was removed via filtration and the filtrate was concentrated under reduced pressure. The residue was purified with reverse phase column chromatography eluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3 to give the desired product as a yellow solid (0.017 g, 26% yield). 1H NMR (500 MHz, DMSO-d6): δ 9.64 (s, 1H), 8.32 (d, J=7.5 Hz, 1H), 7.99 (br, 1H), 7.75-7.49 (m, 4H), 2.63 (m, 1H), 0.72-0.66 (m, 2H), 0.52-0.46 (m, 2H). LCMS (Method A): RT=5.63 min, m/z: 363.0 [M+H+].

Aufarbeitung

  1. customThe mixture was degassed with N2 for 10 minutes
  2. customirradiated in a microwave reactor at 160° C. for 2 hours
  3. customsolid was removed via filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified with reverse phase column chromatography
  6. washeluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3

Quellen und Nachweise

ORD-Eintrag
ord-2e9f37b7b22d444bb84b6b7e6bd7b78e
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697708B2

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