Reaktion #610280

ord-7663a71618584c9f9ac14ad722f6976f

Reaktionsgleichung

COc1nc(Br)ccc1N
6-bromo-2-methoxypyridin-3-amine
Cc1nccn1C
1,2-dimethyl-1H-imidazole
CC(=O)[O-].[K+]
KOAc
COc1nc(-c2cnc(C)n2C)ccc1N
title compound
Ausbeute 16.5%
COc1nc(-c2cnc(C)n2C)ccc1N
6-(1,2-Dimethyl-1H-imidazol-5-yl)-2-methoxypyridin-3-amine
Ausbeute 16.5%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe reaction mixture was filtered
  2. 2
    workup.ADDITIONdiluted with NaCl solution
  3. 3
    Extraktionextracted with EtOAc
  4. 4
    SonstigeThe organic layer was purified
  5. 5
    Waschenby eluting through an SCX-2 column
  6. 6
    Wascheneluting with 0-4% MeOH/EtOAc

Vorschrift

A suspension of 6-bromo-2-methoxypyridin-3-amine (96 mg, 0.473 mmol), 1,2-dimethyl-1H-imidazole (91 mg, 0.946 mmol), Pd(OAc)2 (4.3 mg, 0.019 mmol), KOAc (93 mg, 0.95 mmol) in DMA (3 mL) was stirred at 1500 under microwave irradiation for 8 hours. The reaction mixture was filtered, diluted with NaCl solution and extracted with EtOAc. The organic layer was purified by eluting through an SCX-2 column using 2M NH3/MeOH followed by Biotage silica gel column chromatography eluting with 0-4% MeOH/EtOAc to give the title compound as pink solid (17 mg, 16%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09334286B2uspto-grants-2016_05