tert-butyl (5-cyano-1H-indol-1-yl)acetate synthesis

Yield:1229608-56-3 98%

Reaction Conditions:

with potassium carbonate in acetonitrile; for 16 h;Reflux;

Steps:

1

tert-butyl {5-r(hvdroxyamino)(imino)methvH-1 H-indol-1 -yl)acetate Step 1: tert-butyl (5-cyano-1 H-indol-1 -yl)acetate tert-butyl bromoacetate (0.88 ml 5.99 mmol) was added to a suspension of 5-cyanoindole (0.71 g; 4.99 mmol) and K₂CO₃ (1.38 g; 9.99 mmol) in CH₃CN (20 mL) and the resulting mixture was stirred at reflux for 16 hours. Filtration and concentration in vacuo gave a light yellow oil which crystallized upon standing. The solid was triturated in a mixture of Et₂O and hexane to give the title compound as an off-white solid (1.26 g, 98%). HPLC (Method A), Rt: 4.43 min (Purity: 96.8%). LC/MS (Method B): 256.9 (M+H)⁺.

References:

WO2010/69949,2010,A1 Location in patent:Page/Page column 55