Reaktion #44201

Reaktionsgleichung

PPh3

4-(4-bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (2-cyano-ethyl)-amide

DIAD

TMSN3

→

desired product

Ausbeute 61.0%

3-{5-[4-(4-bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl]-tetrazol-1-yl}-propionitrile

Ausbeute 61.0%

Lösungsmittel

MeCN

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water
2. 2
   ExtraktionThe aqueous layer was extracted with ethyl acetate
3. 3
   TrocknenThe combined organic extracts were dried (MgSO4)
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigePurification by flash column chromatography

Vorschrift

PPh3 (83 mg, 0.32 mmol) was added to a stirred suspension of 4-(4-bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (2-cyano-ethyl)-amide (51 mg, 0.12 mmol) in MeCN (1.5 mL). DIAD (0.065 mL, 0.31 mmol) and TMSN3 (0.045 mL, 0.32) were added dropwise. After 22 hours, the reaction mixture was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography gave clean desired product (33 mg, 61%).

Quelle