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Cesium carbonate → [5-(6-Methoxy-pyridin-3-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanone

HRID 2068652
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2068652
Br[C:2]1[S:6][CH:5]=[C:4]([C:7]([N:9]2[C@@H:18]3[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11][CH2:10]2)=[O:8])[CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][N:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:19][O:20][C:21]1[N:22]=[CH:23][C:24]([C:2]2[S:6][CH:5]=[C:4]([C:7]([N:9]3[CH:18]4[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]4)[CH2:12][CH2:11][CH2:10]3)=[O:8])[CH:3]=2)=[CH:25][CH:26]=1
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Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 86646712HCID 86646712, Verbindung

Produkt 1

HCID 44226877[5-(6-Methoxy-pyridin-3-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 962WaterLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

cis-(5-Bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)methanone (0.1 g, 0.30 mmol) was combined with 2-methoxypyridine-5-boronic acid (0.045 g, 0.3 mmol), caesium carbonate (0.142 g, 0.44 mmol), and palladium tetrakis(triphenylphosphine) (0.031 g, 0.03 mmol) in DME (6 mL), IMS (2 mL) and water (13 mL). The reaction mixture was heated by microwave irradiation to 140° C. for 20 minutes. The solution was partitioned between ethyl acetate and water and the phases separated then the organic phase was dried and evaporated to afford the title compound as a gum. The compound was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were evaporated to give the title compound as an oil (0.077 g). LCMS m/z 357.25 [M+H]+ R.T.=12.46 min (Analytical Method 2).

Aufarbeitung

  1. customThe solution was partitioned between ethyl acetate and water
  2. customthe phases separated
  3. customthe organic phase was dried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a3d40bfc25e640a2ac58c769ca44adfd
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299063B2

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