Tetrafluoroboric acid → HCID 89545229, Verbindung

HRID 1507539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1507539
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1.[CH:11]1(B(O)O)[CH2:13][CH2:12]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[H+].[B-](F)(F)(F)F>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:11]1([C:2]2[CH:3]=[CH:4][C:5]3[S:9][CH:8]=[N:7][C:6]=3[CH:10]=2)[CH2:13][CH2:12]1

Komponenten

9

Edukt 5

HCID 28118Tetrafluoroboric acidHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 36101555-Bromobenzothiazole

Produkt 1

HCID 89545229HCID 89545229, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Following the same procedure in step 1 of Example 344 using 5-bromo-1,3-benzothiazole (500 mg, 2.34 mmol, 1.00 equiv), cyclopropylboronic acid (300 mg, 3.49 mmol, 1.50 equiv), potassium phosphate (2.2 g, 10.36 mmol, 4.50 equiv), palladium acetate (51.6 mg, 0.10 equiv), and PCy3.HBF4 (0.17 g, 0.20 equiv) in a mixture of toluene (12 mL) and water (1.2 mL). The crude product was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (10:1-5:1) to provide the title compound as a purple oil. MS m/z [M+H]+ (ESI): 176.

Aufarbeitung

  1. customThe crude product was purified by flash chromatography on silica gel
  2. washeluting with petroleum ether/ethyl acetate (10:1-5:1)

Quellen und Nachweise

ORD-Eintrag
ord-727c5d0497164b88abc369341db6ab3d
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221809B2

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