StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

1,2-Dimethoxyethane → HCID 67189214, Verbindung

HRID 885996
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 885996
Br[C:2]1[C:3]([O:24][CH3:25])=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[C:14](=[O:22])[NH:15][C:16]([CH3:21])([CH3:20])[CH2:17][C:18]=4[N:19]=3)[C:6]=2[CH:23]=1.Cl.[N:27]1([CH2:33][C:34]2[CH:35]=[C:36](B3OC(C)(C)C(C)(C)O3)[CH:37]=[CH:38][CH:39]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:20][C:16]1([CH3:21])[NH:15][C:14](=[O:22])[C:13]2[S:12][C:11]([N:7]3[C:6]4[CH:23]=[C:2]([C:36]5[CH:37]=[CH:38][CH:39]=[C:34]([CH2:33][N:27]6[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]6)[CH:35]=5)[C:3]([O:24][CH3:25])=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)=[N:19][C:18]=2[CH2:17]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 46739016HCID 46739016, VerbindungHCID 67188040HCID 67188040, Verbindung

Produkt 1

HCID 67189214HCID 67189214, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of Example 490 (0.05 g, 0.118 mmol), 3-(piperidin-1-ylmethyl)-phenylboronic acid pinacol ester hydrochloride (0.0478 g, 0.141 mmol), potassium phosphate (0.1 g, 0.471 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.0082 g, 0.0071 mmol) was degassed under 3 cycles of nitrogen and vacuum. DME (1.2 mL) and water (0.3 ml) were added and the mixture was degassed as before. The mixture was heated to 120° C. under microwave irradiation in a sealed tube for 1 h. Water (15 mL) and DCM (15 mL) were added. The aqueous fraction was separated and extracted with DCM (2×10 mL). The combined organic fractions were filtered through a Whatman 1μ PTFE tube and concentrated in vacuo. The residue was purified by preparative HPLC (Method 6) to give the title compound (0.0243 g, 40%) as a colourless solid. δH (CDCl3) 7.76 (1H, s), 7.45 (1H, s), 7.41-7.31 (2H, m), 7.30-7.25 (1H, m), 6.57 (1H, s), 5.28 (1H, s), 4.37-4.32 (2H, m), 4.21-4.16 (2H, m), 3.78 (3H, s), 3.54 (2H, s), 2.84 (2H, s), 2.49-2.37 (4H, m), 1.64-1.54 (4H, m), 1.48-1.35 (8H, m). LCMS (ES+) 519.3 (M+H)+, RT 2.32 minutes (Method 1).

Aufarbeitung

  1. customthe mixture was degassed as before
  2. additionWater (15 mL) and DCM (15 mL) were added
  3. customThe aqueous fraction was separated
  4. extractionextracted with DCM (2×10 mL)
  5. filtrationThe combined organic fractions were filtered through a Whatman 1μ PTFE tube
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative HPLC (Method 6)

Quellen und Nachweise

ORD-Eintrag
ord-622dbc25561f4ecab65ca5a1fef26e0a
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08242116B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion