Reaktion #1070601

ord-0df4a60dfa7d4ae5a848022d3b6b92f0

Reaktionsgleichung

Brc1cnc(N2CCc3c([nH]c4ccccc34)C2c2ccc3c(c2)CCO3)nc1
2-(5-bromo-2-pyrimidinyl)-1-(2,3-dihydro-5-benzofuranyl)-2,3,4,9-tetrahydro-1H-β-carboline
Cc1nccn1C
1,2-dimethyl-1H-imidazole
c1ccc(P(c2ccccc2)c2ccccc2)cc1
PPh3
O=C([O-])[O-].[K+].[K+]
K2CO3
[Na+].[OH-]
NaOH
Cc1ncc(-c2cnc(N3CCc4c([nH]c5ccccc45)C3c3ccc4c(c3)CCO4)nc2)n1C
title product
Cc1ncc(-c2cnc(N3CCc4c([nH]c5ccccc45)C3c3ccc4c(c3)CCO4)nc2)n1C
1-(2,3-Dihydro-benzofuran-5-yl)-2-[5-(2,3-dimethyl-3H-imidazol-4-yl)-pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-β-carboline

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    ExtraktionThe resulting solution was extracted with CH2Cl2 (3×50 mL)
  2. 2
    Trocknendried over Na2SO4
  3. 3
    SonstigePurification by preparative TLC

Vorschrift

2-(5-bromo-2-pyrimidinyl)-1-(2,3-dihydro-5-benzofuranyl)-2,3,4,9-tetrahydro-1H-β-carboline (0.45 g, 1.00 mmol), 1,2-dimethyl-1H-imidazole (0.18 g, 1.87 mmol), Pd(OAc)2 (12 mg, 0.05 mmol), PPh3 (26 mg, 0.1 mmol) and K2CO3 (0.28 g, 2 mmol) were stirred in 3.5 mL DMF at 140° C. for 14 hours. The mixture was poured into aqueous 10% NaOH solution (50 mL). The resulting solution was extracted with CH2Cl2 (3×50 mL) and dried over Na2SO4. Purification by preparative TLC yielded the title product as yellow powder.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06864253B2uspto-grants-2005_03