Sodium Chloride → HCID 71811360, Verbindung

HRID 714062

Reaktionsgleichung

Reaktionsgleichung von HRID 714062
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([NH2:12])[C:6]=2[CH:5]=[N:4][CH:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)#[N:14].C([O-])([O-])=O.[Na+].[Na+].[Na+].[Cl-]>C(O)C.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>[NH2:12][CH:7]1[C:6]2[CH:5]=[N:4][CH:3]=[C:2]([C:18]3[CH:19]=[CH:20][C:15]([C:13]#[N:14])=[CH:16][CH:17]=3)[C:11]=2[CH2:10][CH2:9][CH2:8]1

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 717433794-Bromo-5,6,7,8-tetrahydroisoquinolin-8-amine

Produkt 1

HCID 71811360HCID 71811360, VerbindungAusbeute 185,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

In a 100 mL round-bottomed flask, (rac)-4-bromo-5,6,7,8-tetrahydroisoquinolin-8-amine (intermediate A-1[D]) (681 mg, 3 mmol) and 4-cyanophenylboronic acid (540 mg, 3.6 mmol) were dissolved in ethanol (54 mL) to give a light brown solution. Na2CO3 (350 mg, 3.3 mmol), dissolved in water (8.9 mL) was added followed by tetrakis(triphenylphosphine)palladium (0) (104 mg, 90 μmol) after evacuation and replacing 5 times with Argon. The solution was then heated at 85° C. overnight. The reaction was treated with an aq. 10% NaCl solution and extracted with AcOEt (3×). The organic phases were washed again with an aq. 10% NaCl solution, dried over Na2SO4, filtered and evaporated under reduced pressure to give 1.39 g brown foam which was purified by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (5 to 7.5%)) and precipitated from CH2Cl2 with n-pentane to give the title compound (605 mg, 81%) as a light brown foam. MS: 250.1 (M+H+).

Aufarbeitung

  1. customto give a light brown solution
  2. additionwas added
  3. extractionextracted with AcOEt (3×)
  4. washThe organic phases were washed again with an aq. 10% NaCl solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9eb7cc79a46d46eabc3b3548630f4413
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187429B2

Verknüpfte Notizen

Wird geladen…