Reaktion #1596476

Reaktionsgleichung

Tert-butyl (1-(4-(7-bromo-1-methyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate

pyridin-3-yl boronic acid

triphenylphosphine

cesium fluoride

→

title compound

Ausbeute 21.1%

Tert-butyl (1-(4-(1-methyl-2-oxo-7-(pyridin-3-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate

Ausbeute 21.1%

Lösungsmittel

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give an orange solution
2. 2
   SonstigeThe reaction mixture was degassed
3. 3
   Sonstigeby bubbling nitrogen for 10 minutes
4. 4
   SonstigeThe resulting reaction
5. 5
   Sonstigewas degassed
6. 6
   EinengenThe reaction mixture was concentrated to dryness under reduced pressure
7. 7
   SonstigeThe crude was purified by preparatory HPLC

Vorschrift

Tert-butyl (1-(4-(7-bromo-1-methyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (57 mg, 0.117 mmol), pyridin-3-yl boronic acid (21.52 mg, 0.175 momol), triphenylphosphine (9.18 mg, 0.035 mmol), cesium fluoride (89 mg, 0.584 mmol) were dissolved in 1,2-dimethoxyethane (2 ml) to give an orange solution. The reaction mixture was degassed by bubbling nitrogen for 10 minutes. Palladium(II)acetate (3.93 mg, 0.018 mmol) was added at room temperature. The resulting reaction was degassed and heated to 80° C. for 18 hours. The reaction mixture was concentrated to dryness under reduced pressure. The crude was purified by preparatory HPLC to give the title compound (12 mg, 21%). LCMS (Method D) RT 1.158 min, M+1=487. 1H NMR (500 MHz, CDCl3): 7.64-7.52 (1H, m), 7.37-7.21 (8H, m), 4.94 (2H, s), 3.43 (3H, s), 2.59-2.36 (4H, m), 2.15-2.01 (1H, m), 1.91-1.77 (1H, m), 1.47-1.20 (9H, br s).

Quelle