Reaktion #304145

Reaktionsgleichung

(S)-tert-Butyl 4-(1-amino-1-oxo-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

4-bromo-2-methoxypyridine

sodium carbonate

→

sub-titled compound

Ausbeute 88.8%

(S)-tert-Butyl 4-(1-amino-3-(4-(2-methoxypyridin-4-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Ausbeute 88.8%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas bubbled through the mixture
2. 2
   workup.ADDITION1,1 bis(Di-tert-butylphosphino)ferrocene palladium dichloride (5 mg) was added
3. 3
   SonstigeThe mixture was evaporated onto silica
4. 4
   Sonstigepurified by chromatography on silica eluting with ethyl acetate

Vorschrift

(S)-tert-Butyl 4-(1-amino-1-oxo-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 16, step (i), 250 mg) and 4-bromo-2-methoxypyridine (91 mg) in acetonitrile (8 mL) were treated with aqueous sodium carbonate solution (2M, 0.5 mL) and nitrogen was bubbled through the mixture. 1,1 bis(Di-tert-butylphosphino)ferrocene palladium dichloride (5 mg) was added and the mixture was heated at 85° C. for 18 h. The mixture was evaporated onto silica and purified by chromatography on silica eluting with ethyl acetate to afford the sub-titled compound (214 mg).

Quelle