Water → HCID 86698767, Verbindung

HRID 1054777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054777
Br[C:2]1[CH:13]=[CH:12][C:5]2[O:6][C@H:7]([CH2:10][OH:11])[CH2:8][O:9][C:4]=2[CH:3]=1.[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[CH:20][NH:21]2)=[CH:17][C:16]=1B1OCC(C)(C)CO1.[C:32](=O)([O-])[O-:33].[K+].[K+].O>CN(C=O)C.O1CCOCC1.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].C(Cl)Cl>[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([CH:32]=[O:33])=[CH:20][NH:21]2)=[CH:17][C:16]=1[C:2]1[CH:13]=[CH:12][C:5]2[O:6][C@H:7]([CH2:10][OH:11])[CH2:8][O:9][C:4]=2[CH:3]=1

Komponenten

9

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 46942285[(2R)-6-Bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanolHCID 866987336-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole

Produkt 1

HCID 86698767HCID 86698767, VerbindungAusbeute 141,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of [(2R)-6-bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.54 g, 2.05 mmol) (which can be prepared as in Biorg. Med. Chem. 2007, 15, 4048.), 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (0.52 g, 4.06 mmol) in DMF (4 mL) and dioxane (4 mL) was stirred at room temperature for 30 min. under N2. Pd(dppf)Cl2 (100 mg, 0.137 mmol) and 2 N potassium carbonate (10 mL, 20 mmol) was added. The resulting mixture was stirred for 30 min. at 90° C. under N2. TLC showed the reaction was complete. Water (50 mL) and methylene chloride (50 mL) was added. The aqueous layer was extracted with methylene chloride (30 mL×3). The combined organic layer was dried over sodium sulfate, filtered and evaporated to give the title compound (1 g) which was used in the next step without further purification.

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 30 min. at 90° C. under N2
  2. extractionThe aqueous layer was extracted with methylene chloride (30 mL×3)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2e8fa3c00ff745cda30570598101ac54
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394285B2

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