Dichloromethane → 3-(6-Aminopyridin-2-yl)-4-methyl-N-[3-(trifloromethyl)phenyl]benzamide

HRID 77728

Reaktionsgleichung

Reaktionsgleichung von HRID 77728
I[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)=[O:6].C([O-])(=O)C.[K+].CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+].Br[C:55]1[N:60]=[C:59]([NH2:61])[CH:58]=[CH:57][CH:56]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.CN(C=O)C>[NH2:61][C:59]1[N:60]=[C:55]([C:2]2[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=2[CH3:21])[C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[O:6])[CH:56]=[CH:57][CH:58]=1

Komponenten

10

Edukt 6

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 3008092-Amino-6-bromopyridineHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 171975693-iodo-4-methyl-N-(3-(trifluoromethyl)phenyl)benzamide

Produkt 1

HCID 690476313-(6-Aminopyridin-2-yl)-4-methyl-N-[3-(trifloromethyl)phenyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a degassed mixture of 3-iodo-4-methyl-N-[3-(trifluoromethyl)phenyl]benzamide (0.500 g, 1.23 mmol), potassium acetate (424 mg, 4.32 mmol), DMF (15 mL), and 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2]bi[[1,3,2]dioxaborolanyl] (0.329 g, 1.30 mmol) was added [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with DCM (1:1) (101 mg, 0.123 mmol). The reaction was heated to 80° C. for 3 hours, at which time conversion to the boronic ester was complete. The mixture was cooled and potassium carbonate (512 mg, 3.70 mmol), water (2.24 mL), and 6-bromopyridin-2-amine (214 mg, 1.23 mmol) were added. After degassing the mixture, it was heated to 85° C. for 1 hour. The solvent was then removed in vacuo. Water was added and the product was extracted with three portions of ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated. Purification was carried out by flash column chromatography (eluting with a gradient from 0-50% ethyl acetate in hexanes) afforded the product. (254 mg, 50%).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. customAfter degassing the mixture, it
  3. customThe solvent was then removed in vacuo
  4. additionWater was added
  5. extractionthe product was extracted with three portions of ethyl acetate
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customPurification
  10. washeluting with a gradient from 0-50% ethyl acetate in hexanes)
  11. customafforded the product

Quellen und Nachweise

ORD-Eintrag
ord-fbb3af39a7c34521ab72c521080a6978
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841318B2

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