Sodium Carbonate → HCID 67973310, Verbindung

HRID 1184696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184696
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19](B4OC(C)(C)C(C)(C)O4)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].Br[C:32]1[CH:37]=[CH:36][C:35]([S:38][CH3:39])=[CH:34][C:33]=1[CH3:40].C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:32]4[CH:37]=[CH:36][C:35]([S:38][CH3:39])=[CH:34][C:33]=4[CH3:40])[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:11][CH2:12]1)=[O:6])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 26370189(4-Bromo-3-methylphenyl)(methyl)sulfaneHCID 67973765HCID 67973765, Verbindung

Produkt 1

HCID 67973310HCID 67973310, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a mixture of 4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid isopropyl ester (150 mg), 1-bromo-2-methyl-4-methylsulfanyl-benzene (60 mg), in N,N-dimethylformamide (3 mL) a 2 M aqueous Na2CO3 solution (0.29 mL) is added. The mixture is sparged with argon for 10 min and PdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (19 mg) is added. The resulting mixture is stirred for 6 h at 90° C. After cooling to room temperature, water and methanol are added and the aqueous phase is extracted with ethyl acetate. The organic phase is concentrated and the residue is purified by HPLC on reversed phase (MeOH/H2O/TFA). Yield: 56 mg (56% of theory); LC (method 2): tR=1.70 min; Mass spectrum (ESI+): m/z=426 [M+H]+.

Aufarbeitung

  1. customThe mixture is sparged with argon for 10 min
  2. additionPdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (19 mg) is added
  3. temperatureAfter cooling to room temperature
  4. additionwater and methanol are added
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. concentrationThe organic phase is concentrated
  7. customthe residue is purified by HPLC on reversed phase (MeOH/H2O/TFA)

Quellen und Nachweise

ORD-Eintrag
ord-2b250d6587684415a512c5dc60611b13
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669271B2

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