Cesium carbonate → HCID 86648952, Verbindung

HRID 449887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449887
Br[C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:18])[C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])[CH:5]=[CH:4][N:3]=1.[Cl:19][C:20]1[N:25]=[C:24]([NH2:26])[CH:23]=[C:22]([CH:27]([CH3:29])[CH3:28])[N:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>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].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.COCCOC>[Cl:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([Cl:16])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:26][C:24]2[CH:23]=[C:22]([CH:27]([CH3:28])[CH3:29])[N:21]=[C:20]([Cl:19])[N:25]=2)[CH:7]=1)=[O:18]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 735550432-Chloro-6-isopropylpyriMidin-4-aMineHCID 75464886N-(2-Bromopyridin-4-yl)-2,6-dichlorobenzamide

Produkt 1

HCID 86648952HCID 86648952, VerbindungAusbeute 117,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a microwave tube was added N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (0.25 g, 0.72 mmol), 2-chloro-6-isopropylpyrimidin-4-amine (0.16 g, 0.94 mmol), Pd2(dba)3 (0.020 g, 0.022 mmol), XantPhos (0.008 g, 0.014 mmol), Cs2CO3 (0.47 g, 1.4 mmol) dioxane (20 mL) and DME (5 mL). The mixture was degassed with N2 for 10 min. The resulting mixture was irradiated in a microwave reactor at 130° C. for 2 hours and then cooled to room temperature. The mixture was filtered through Celite and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc/Petrolum ether=20/80 to 30/70) to give 2,6-dichloro-N-(2-(2-chloro-6-isopropylpyrimidin-4-ylamino)pyridin-4-yl)benzamide (370 mg, yield: 90%). LCMS (ESI) m/z: 436.0 [M+H+].

Aufarbeitung

  1. customThe mixture was degassed with N2 for 10 min
  2. customThe resulting mixture was irradiated in a microwave reactor at 130° C. for 2 hours
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (EtOAc/Petrolum ether=20/80 to 30/70)

Quellen und Nachweise

ORD-Eintrag
ord-1dc9c1dd59374bdf9455eee1c09050c4
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486950B2

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