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Cesium carbonate → HCID 71115228, Verbindung

HRID 1502311
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1502311
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21](B2OCC(C)(C)CO2)[CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.O.[Pd](Cl)Cl.C(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)(C)C.C(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)(C)C>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[C:25]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([NH:12][C:13]([CH:15]4[CH2:17][CH2:16]4)=[O:14])[N:8]=[CH:9]3)=[CH:4][CH:3]=2)[CH:26]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 115143254-Chloro-2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrileHCID 67974626N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide

Produkt 1

HCID 71115228HCID 71115228, VerbindungAusbeute 5,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11714597
Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)
Katalysator
HCID 962WaterLösungsmittel
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide (200 mg, 0.68 mmol), 4-chloro-2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile (205 mg, 0.816 mmol), cesium carbonate (0.22 g, 0.68 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine) palladium dichloride (24.0 mg, 0.05 eq) in a mixture of acetonitrile and water (10 mL, 10:1) was purged with nitrogen and stirred at 90° C. for 45 minutes under microwave irradiation. Ethyl acetate (20 mL) was added to the reaction mixture and it was filtered. The solid was extracted with ethyl acetate (20 mL×4). The combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by HPLC separation to give the product (13.7 mg, 5.8%). LCMS (ESI): RT (min)=1.099, M+H+=347.9, method=A. 1H NMR (400 MHz, DMSO-d6) δ 11.04 (s, 1H), 9.24 (s, 1H), 8.54 (s, 1H), 8.33 (t, J=0.8 Hz, 1H), 8.08-7.72 (m, 5H), 2.09-2.05 (m, 1H), 0.88-0.83 (m, 4H).

Aufarbeitung

  1. customwas purged with nitrogen
  2. additionEthyl acetate (20 mL) was added to the reaction mixture and it
  3. filtrationwas filtered
  4. extractionThe solid was extracted with ethyl acetate (20 mL×4)
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by HPLC separation

Quellen und Nachweise

ORD-Eintrag
ord-08a3ce2b31ca4789aaf8eb0595acd6f8
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09206175B2

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