Sodium Chloride → (rac)-6-(7-Amino-6,7-dihydro-5H-cyclopenta[c]pyridin-4-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-one

HRID 530327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530327
Br[C:2]1[C:3]2[CH2:10][CH2:9][CH:8]([NH2:11])[C:4]=2[CH:5]=[N:6][CH:7]=1.[CH3:12][N:13]1[C:22]2[C:17](=[CH:18][C:19](B3OC(C)(C)C(C)(C)O3)=[CH:20][CH:21]=2)[CH2:16][CH2:15][C:14]1=[O:32].C([O-])([O-])=O.[Na+].[Na+].[Na+].[Cl-]>CCO.O.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>[NH2:11][CH:8]1[C:4]2[CH:5]=[N:6][CH:7]=[C:2]([C:19]3[CH:18]=[C:17]4[C:22](=[CH:21][CH:20]=3)[N:13]([CH3:12])[C:14](=[O:32])[CH2:15][CH2:16]4)[C:3]=2[CH2:10][CH2:9]1

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 717438934-Bromo-6,7-dihydro-5H-cyclopenta[C]pyridin-7-amineHCID 722082331-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 89456204(rac)-6-(7-Amino-6,7-dihydro-5H-cyclopenta[c]pyridin-4-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-oneAusbeute 14,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

In a 50 ml round-bottomed flask, (rac)-4-bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-amine (intermediate A-3[C]) (107 mg, 500 μmol) and 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one (intermediate A-1) (172 mg, 600 μmol) were dissolved in EtOH (9 mL) to give a brown solution. Na2CO3 (58.3 mg, 550 μmol), dissolved in water (1.5 mL) was added followed by tetrakis(triphenylphosphine)palladium (0) (17.3 mg, 15.0 mmol) after evacuation and replacing 5 times with Argon. The suspension was then heated at 85° C. overnight. A aq. 10% NaCl solution was added at RT, and the mixture was extracted with AcOEt (3×). The organic fractions were washed again with aq. 10% NaCl solution, dried over Na2SO4, filtered, evaporated and purified by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (2%)) to afford the title compound (21 mg, 14%) as a dark green powder. MS: 294.2 (M+H+)

Aufarbeitung

  1. customto give a brown solution
  2. additionwas added
  3. extractionthe mixture was extracted with AcOEt (3×)
  4. washThe organic fractions were washed again with aq. 10% NaCl solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (2%))

Quellen und Nachweise

ORD-Eintrag
ord-3f028aaaf65342fea1d1873e6bf79007
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353081B2

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