Potassium Carbonate → (1-(5-(4-Methoxypyridin-2-yl)pyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone

HRID 630482

Reaktionsgleichung

Reaktionsgleichung von HRID 630482
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:16][S:17][C:18]1[C:26]2[C:21](=[CH:22][C:23]([C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:28])=[CH:24][CH:25]=2)[N:20]([C:35]2[N:40]=[CH:39][C:38](B3OC(C)(C)C(C)(C)O3)=[CH:37][N:36]=2)[CH:19]=1>CN(C=O)C.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:38]2[CH:39]=[N:40][C:35]([N:20]3[C:21]4[C:26](=[CH:25][CH:24]=[C:23]([C:27]([N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)=[O:28])[CH:22]=4)[C:18]([S:17][CH3:16])=[CH:19]3)=[N:36][CH:37]=2)[CH:7]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 47384842-Bromo-4-methoxypyridineHCID 131735394(3-(Methylthio)-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)-1H-indol-6-yl)(morpholino)methanone

Produkt 1

HCID 118676926(1-(5-(4-Methoxypyridin-2-yl)pyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Bromo-4-methoxypyridine (215 mg, 1.145 mmol, 1.1 eq), potassium carbonate (431 mg, 3.124 mmol, 3.0 eq) and PdCl2(dppf) (85 mg, 0.104 mmol, 0.1 eq) were added at room temperature and under an inert atmosphere to a solution of the raw product from 141a) (500 mg, 1.041 mmol, 1.0 eq) in DMF (10 mL). The reaction mixture was stirred at 100° C. for 3 h and then cooled to room temperature. For the work up, the mixture was diluted with ethyl acetate (20 mL), washed with water (2×20 mL) and brine, and dried over anhydrous sodium sulfate. The solvents were removed under reduced pressure and the remnant was purified by column chromatography [100-200 mesh silica gel; 5% methanol in dichloromethane]. White solid. Yield: 200 mg (41% of theory over two steps)

Aufarbeitung

  1. temperaturecooled to room temperature
  2. washwashed with water (2×20 mL) and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvents were removed under reduced pressure
  5. customthe remnant was purified by column chromatography [100-200 mesh silica gel; 5% methanol in dichloromethane]

Quellen und Nachweise

ORD-Eintrag
ord-e7a68aef7859434f87b155f8909a692a
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315490B2

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