Water → 3-imidazo[1,2-a]pyridine-7-yl-N-methyl-benzamide

HRID 383303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 383303
Br[C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:11][NH:12][C:13]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)=[O:14].O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:10]1[CH:9]=[CH:8][N:5]2[CH:6]=[CH:7][C:2]([C:19]3[CH:20]=[C:15]([CH:16]=[CH:17][CH:18]=3)[C:13]([NH:12][CH3:11])=[O:14])=[CH:3][C:4]=12

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27735243-(Methylcarbamoyl)benzeneboronic acidHCID 150989037-Bromoimidazo(1,2-a)pyridine

Produkt 1

HCID 684844493-imidazo[1,2-a]pyridine-7-yl-N-methyl-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

7-Bromo-imidazo-[1,2-a]-pyridine (1 eq, 0.5 mmol, 100 mg) and (3-methylamino carbonylphenyl)boronic acid (1.1 eq, 0.558 mmol, 99.9 mg) are dissolved in DME (3 ml) and water (0.8 ml) and Na2CO3 (3 eq, 1.52 mmol, 161 mg) is added. PdCl2(PPh3)2 (0.05 eq, 0.025 mmol, 17.8 mg) is then added and the reaction mixture is heated using microwave radiation at 120° C. for 10 min. At the completion of this time the solvent is removed in vacuo and the reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to yield 3-imidazo[1,2-a]pyridine-7-yl-N-methyl-benzamide as a brown solid; [M+H]+=252

Aufarbeitung

  1. temperaturethe reaction mixture is heated
  2. customat 120° C.
  3. customfor 10 min
  4. customAt the completion of this time the solvent is removed in vacuo
  5. customthe reaction mixture is purified by flash column chromatography
  6. washeluting with 9:1 DCM/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-b91d90e9ac9f49029ba0eea0655cce7b
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367662B2

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