Potassium Carbonate → 8-(Benzyloxy)-2-(7-ethylimidazo[1,2-a]pyridin-3-yl)quinoline

HRID 1095739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095739
[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[CH:10][N:11]=[C:5]2[CH:4]=1)[CH3:2].[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[C:27](Cl)[CH:26]=[CH:25]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[C:27]([C:9]1[N:6]3[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][C:5]3=[N:11][CH:10]=1)[CH:26]=[CH:25]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 181844637-Ethylimidazo[1,2-a]pyridineHCID 220422348-(Benzyloxy)-2-chloroquinoline

Produkt 1

HCID 667814498-(Benzyloxy)-2-(7-ethylimidazo[1,2-a]pyridin-3-yl)quinolineAusbeute 112,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 7-ethylimidazo[1,2-a]pyridine (1.18 g, 8.06 mmol), 8-benzyloxy-2-chloroquinoline (2.17 g, 8.06 mmol), potassium carbonate (2.23 g, 16.2 mmol), palladium (II) acetate (90.5 mg, 0.40 mmol), tetrakis(triphenylphosphine)palladium (0) (466 mg, 0.40 mmol), 1,4-dioxane (33 ml) and water (0.33 ml) was heated under a nitrogen atmosphere overnight. The reaction mixture was diluted with water, extracted with CH2Cl2 and EtOAc, and the combined organic extracts were dried over Na2SO4, filtered and concentrated to afford the desired product (3.45 g) as a solid. MS APCI (+) m/z 380.2 (M+1) detected.

Aufarbeitung

  1. temperaturewas heated under a nitrogen atmosphere overnight
  2. extractionextracted with CH2Cl2 and EtOAc
  3. dry with materialthe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c8670632d03d4a3e83be8ca1536c8b24
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138181B2

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