tert-Butyl piperazine-1-carboxylate → 4-[2-(2-Hydroxy-ethyl)-1-oxo-1,2-dihydro-isoquinolin-7-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 2068594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2068594
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([CH2:13][CH2:14][OH:15])[C:9]2=[O:12])=[CH:4][CH:3]=1.[N:16]1([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:25]([O:24][C:22]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][N:8]([CH2:13][CH2:14][OH:15])[C:9]3=[O:12])=[CH:4][CH:3]=2)[CH2:18][CH2:17]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Komponenten

7

Edukt 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23665647Potassium tert-butoxideHCID 592382027-Bromo-2-(2-hydroxyethyl)-isoquinolin-1-one

Produkt 1

HCID 592381654-[2-(2-Hydroxy-ethyl)-1-oxo-1,2-dihydro-isoquinolin-7-yl]piperazine-1-carboxylic acid tert-butyl esterAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of compound 6 (6.8 g, 25.4 mmol), tert-butyl piperazine-1-carboxylate (5.68 g, 30.5 mmol), Pd2(dba)3 (775 mg, 0.85 mmol), S-Phos (1.16 g) and t-BuOK (5.7 g, 50.8 mmol) in toluene (100 mL) was heated to 90° C. under nitrogen overnight. Then the mixture was cooled to room temperature and filtered. The filtrate was concentrated, the residue was dissolved in methylene chloride, washed with water, dried (sodium sulfate), concentrated and purified by flash column chromatography (silica gel) to give 7 (6.1 g, 64%)

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with water
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-bb9add7ce3014d93859927942e6edd2f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299023B2

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