2-(Tributylstannyl)pyrimidine → 4-(4-Pyrimidin-2-yl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1157179

Reaktionsgleichung

Reaktionsgleichung von HRID 1157179
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=1)CCC>COCCOC.CCOC(C)=O.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:27]3[N:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 2

HCID 27632512-(Tributylstannyl)pyrimidineHCID 11210451Tert-butyl 4-((4-bromophenyl)amino)piperidine-1-carboxylate

Produkt 1

HCID 589851534-(4-Pyrimidin-2-yl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 13169693Triphenylphosphine palladium dichlorideKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4-(4-Bromo-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (355 mg; 1.002 mmol); 2-tributylstannanyl-pyrimidine (1.1 g; 2.98 mmol); triphenylphosphine palladium dichloride (35 mg, 0.049 mmol) was stirred in DME (4 ml) at 100° C. overnight. Reaction mixture was cooled to room temperature, diluted with EtOAc (100 ml) and water (50 ml). Separated organic layer, washed with brine, dried over Na2SO4, then chromatographed on silica gel eluting with 70% v/v EtOAc/Hexanes yielding product at solid (110 mg; 31%)

Aufarbeitung

  1. customReaction mixture
  2. washSeparated organic layer, washed with brine
  3. dry with materialdried over Na2SO4
  4. customchromatographed on silica gel eluting with 70% v/v EtOAc/Hexanes yielding product at solid (110 mg; 31%)

Quellen und Nachweise

ORD-Eintrag
ord-e64e5671e6d8479f8d65628f7c062c9c
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807672B2

Verknüpfte Notizen

Wird geladen…