Reaktion #546201

Reaktionsgleichung

[(5R)-3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

Intermediate 13

N-({(5S)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide

potassium carbonate

N-({(5S)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide

Intermediate 12

[(5R)-3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

→

N-{[(5S)-3-(3-Fluoro-4-{6-[(5R)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide

Lösungsmittel

DMF

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solids formed
2. 2
   Sonstigewere collected
3. 3
   Waschenrinsed with water
4. 4
   Waschenwashed with dichloromethane
5. 5
   Sonstigedried under vaccum
6. 6
   Sonstigecollected as the title compound (0.42 g)

Vorschrift

[(5R)-3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol (Intermediate 12, 0.5 g, 1.95 mmol), (0.35 g, 0.9 mmol), potassium carbonate (0.622 g, 4.5 mmol), N-({(5S)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (Intermediate 13, 0.736 g, 1.95 mmol) and tetrakis(triphenylphosphino)palladium(0) (0.225 g, 0.195 mmol) were combined and suspended in DMF (7 ml) and water (1 ml). The mixture was heated at 75° C. for 2 hours, then was poured into cold water (30 ml). The solids formed were collected, rinsed with water and washed with dichloromethane, dried under vaccum and collected as the title compound (0.42 g)

Quelle