Cesium carbonate → Methyl 3-hexylquinoline-8-carboxylate

HRID 472791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472791
FC(F)(F)S(O[C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[C:17]([O:19][CH3:20])=[O:18])(=O)=O.[CH2:23](B(O)O)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.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>[CH2:23]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[C:17]([O:19][CH3:20])=[O:18])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 351064Hexylboronic Acid (contains varying amounts of Anhydride)HCID 58056975Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate

Produkt 1

HCID 66660858Methyl 3-hexylquinoline-8-carboxylateAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate (538 mg, 1.6 mmol), hexylboronic acid (415 mg, 3.2 mmol) and Cs2CO3 (779 mg, 2.4 mmol) were suspended in toluene (30 mL). The mixture was purged with nitrogen then tetrakis(triphenylphosphine)palladium (0) (55 mg, 0.05 mmol) was added. The reaction was sealed and heated at 95° C. for 16 h. The mixture was cooled and filtered through celite, rinsing with excess CH2Cl2. The filtrate was concentrated in vacuo. The resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether) to afford 178 mg (41%) of methyl 3-hexylquinoline-8-carboxylate.

Aufarbeitung

  1. customThe mixture was purged with nitrogen
  2. customThe reaction was sealed
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. washrinsing with excess CH2Cl2
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-c7de980b234a48279a603d7e7bc23c14
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633220B2

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