tert-Butyl piperazine-1-carboxylate → tert-Butyl 4-(isoquinolin-5-yl)piperazine-1-carboxylate

HRID 459830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459830
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:58]([O:62][C:63]([N:65]1[CH2:70][CH2:69][NH:68][CH2:67][CH2:66]1)=[O:64])([CH3:61])([CH3:60])[CH3:59].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:58]([O:62][C:63]([N:65]1[CH2:70][CH2:69][N:68]([C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][N:6]=[CH:7]3)[CH2:67][CH2:66]1)=[O:64])([CH3:61])([CH3:59])[CH3:60]

Komponenten

8

Edukt 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 7364875-BromoisoquinolineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 21070949tert-Butyl 4-(isoquinolin-5-yl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5-Bromoisoquinoline (1.37 g) from Step 1 was dissolved in 10 mL of toluene. To this solution was added palladium acetate (74 mg), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (205 mg), 1-(tert-butoxycarbonyl)piperazine (1.29 g) and sodium tert-butoxide (885 mg). This reaction mixture was heated to 100° C. for 8 hours and then allowed to cool to room temperature. The cooled reaction mix was diluted with ethyl acetate (EtOAc) and washed with water, and the organic layer was separated, dried over magnesium sulfate (MgSO4), and concentrated in vacuo. The resulting residue was chromatographed to yield 4-isoquinoline-5-yl-piperazine-1-carboxylic acid tert-butyl ester as 1.5 g of a white solid.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customThe cooled reaction
  3. additionmix
  4. washwashed with water
  5. customthe organic layer was separated
  6. dry with materialdried over magnesium sulfate (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-61939400dbce484b9a70d39c46e1a9e2
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196088B2

Notizen zur Reaktion

Wird geladen…