(2H-1,3-benzodioxol-5-yl)boronic acid → HCID 71226745, Verbindung

HRID 713454

Reaktionsgleichung

Reaktionsgleichung von HRID 713454
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](B(O)O)=[CH:9][C:4]=2[O:3][CH2:2]1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([C:26](SC2C=CC=CC=2)=[O:27])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>C1COCC1.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].S1C=CC=C1C([O-])=O.[Cu+]>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([C:26]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)=[O:27])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Komponenten

6

Edukt 2

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 893758004-Phenylsulfanylcarbonyl-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 71226745HCID 71226745, VerbindungAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 11194830Cuprous 2-thiophenecarboxylateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of benzo[d][1,3]dioxol-5-ylboronic acid (0.39 g, 2.30 mmol), ligand TFP (0.07 g, 0.3 mmol), Pd2dba3 (0.14 g, 0.16 mmol), copper (I) thiophene-2-carboxylate (0.45 g, 2.4 mmol) was added a solution of 4-phenylsulfanylcarbonyl-piperidine-1-carboxylic acid tert-butyl ester (0.5 g, 1.6 mmol) in 10 mL of THF while purging with N2 at 50° C. After 18 hours the reaction mixture was diluted with ethyl acetate, filtered through celite then concentrated in vacuo. Purification by flash chromatography gave the title compound (0.52 g, 1.48 mmol). MS (ESI) m/z 333.8 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.52 min.

Aufarbeitung

  1. customwhile purging with N2 at 50° C
  2. additionAfter 18 hours the reaction mixture was diluted with ethyl acetate
  3. filtrationfiltered through celite
  4. concentrationthen concentrated in vacuo
  5. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c6eab6fe05664f54b7be1505481fadad
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181266B2

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