Potassium Phosphate, Tribasic → 4-(7-Pyridin-3-yl-imidazo[1,2-a]pyridin-3-yl)-phenylamine

HRID 1446663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446663
Cl[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:2]2[CH:7]=[CH:6][N:5]3[C:8]([C:11]4[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=4)=[CH:9][N:10]=[C:4]3[CH:3]=2)[CH:19]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 27343783-Pyridinylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl2×HCID 685394114-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenylamine

Produkt 1

HCID 685456764-(7-Pyridin-3-yl-imidazo[1,2-a]pyridin-3-yl)-phenylamineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a round bottomed flask add 4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-phenylamine (0.5 g, 2.1 mmol), pyridine-3-boronic acid (0.38 g, 1.5 equiv.), potassium phosphate (0.87 g, 2 equiv.), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (also called S-Phos, 0.105 g, 0.125 equiv.), 1,4-dioxane (10 mL), and water (5 mL). Deoxygenate this mixture thoroughly with N2 then add palladium (II) acetate (23 mg, 0.05 equiv.) and reflux the reaction overnight. Concentrate the reaction to dryness and slurry in DCM. Filter this slurry thru Celite® and wash with DCM. Concentrate the filtrate then purify by silica plug (EtOAc to 5% MeOH: DCM to 10% MeOH: DCM) to give a yellow solid (0.39 g, 66%). MS (ES), m/z 287 (M+1).

Aufarbeitung

  1. customDeoxygenate this mixture thoroughly with N2
  2. customthe reaction overnight
  3. concentrationConcentrate
  4. customthe reaction to dryness and slurry in DCM
  5. filtrationFilter this slurry thru Celite®
  6. washwash with DCM
  7. concentrationConcentrate the filtrate
  8. customthen purify by silica plug (EtOAc to 5% MeOH: DCM to 10% MeOH: DCM)

Quellen und Nachweise

ORD-Eintrag
ord-d015bfcd3fb54a4ca7068713dc0e860c
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666879B2

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