Potassium Carbonate → 4-[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-butyramide

HRID 1446675

Reaktionsgleichung

Reaktionsgleichung von HRID 1446675
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[O:19])=[CH:11][CH:10]=2)O1.[Cl:32][C:33]1[CH:38]=[CH:37][N:36]2[C:39](I)=[CH:40][N:41]=[C:35]2[CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.ClCCl.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>[Cl:32][C:33]1[CH:38]=[CH:37][N:36]2[C:39]([C:9]3[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=4)=[O:19])=[CH:13][CH:14]=3)=[CH:40][N:41]=[C:35]2[CH:34]=1

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 574976977-Chloro-3-iodoimidazo[1,2-a]pyridineHCID 685460734-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-butyramide

Produkt 1

HCID 685428324-[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-butyramideAusbeute 62,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Suspend 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-butyramide (0.47 g, 1.15 mmol), 7-chloro-3-iodo-imidazo[1,2-a]pyridine (0.29 g, 1.05 mmol) and solid potassium carbonate (0.48 g, 3.45 mmol) in dioxane (4 mL) and water (2 mL). Deoxygenate the reaction contents with nitrogen for 10 minutes at room temperature. Add trans-dichlorobis(triphenylphosphine)palladium (II) (22 mg, 0.03 mmol) to the reaction. Fit a reflux condenser and heat the reaction to 105° C. over the weekend. Cool the reaction, dilute with dichloromethane and filter through Celite®. Concentrate the filtrate and then chromatograph on silica, using 0-3% methanol/ethyl acetate, to yield the product (301 mg, 57%). MS(ES), m/z 458 (M+1).

Aufarbeitung

  1. customDeoxygenate
  2. customthe reaction contents with nitrogen for 10 minutes at room temperature
  3. temperatureheat
  4. customthe reaction to 105° C. over the weekend
  5. temperatureCool
  6. customthe reaction
  7. filtrationfilter through Celite®
  8. concentrationConcentrate the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-66b40ce91cb54be4a6ddfcea1e681aaa
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666879B2

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