Potassium Phosphate, Tribasic → 6-Cyclopropyl-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline

HRID 13666

Reaktionsgleichung

Reaktionsgleichung von HRID 13666
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:5]2[N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.[CH:23]1(B(O)O)[CH2:25][CH2:24]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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>[CH:23]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([CH3:12])[C:6]([S:13]([CH3:16])(=[O:14])=[O:15])=[C:5]3[N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:25][CH2:24]1

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 120018106-Bromo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline2×

Produkt 1

HCID 120018056-Cyclopropyl-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinolineAusbeute 22,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

6-Bromo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline (compound of example 6) (0.5 g, 1.3 mmol), cyclopropyboronic acid (0.167 g, 1.95 mmol), potassium phosphate tribasic (0.826 g, 3.89 mmol) and tetrakis(triphenylphosphine)palladium(0) (45 mg, 0.039) were mixed together in dioxane (7 mL) and heated at reflux under argon for 8 h. After extraction with dichloromethane and half-saturated NaCl solution, the crude product was purified chromatography on silica gel in dichloromethane/ethyl acetate with a gradient from 100:0 to 90:10. One obtained 0.1 g (21%) of white crystals. MS: m/z=347 (M+H).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux under argon for 8 h
  3. extractionAfter extraction with dichloromethane and half-saturated NaCl solution
  4. customthe crude product was purified chromatography on silica gel in dichloromethane/ethyl acetate with a gradient from 100:0 to 90:10

Quellen und Nachweise

ORD-Eintrag
ord-e3a5e222f59c484bab90c43770ac50bc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728142B2

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