5-fluoro-1-propyl-1H-indole-3-carbaldehyde synthesis

Yield:944465-16-1 88%

Reaction Conditions:

Stage #1: 5-fluoro-1H-indole-3-carbaldehydewith sodium hydride in N,N-dimethyl-formamide;oil at 20; for 0.5 h;
Stage #2: 1-iodo-propane at 20; for 2 h;

Steps:

A4.a

a) Preparation of intermediate 9 Sodium hydride (0.0026 mol, 60% in oil) was added portionwise to a solution of 5- fluoro-1H-indole-3-carboxaldehyde (0.0024 mol) in DMF (8ml) under N₂ flow. The mixture was stirred at room temperature for 30 minutes. 1-Iodopropane (0.0029 mol) was added dropwise. The mixture was stirred at room temperature for 2 hours and poured onto ice water. The precipitate was filtered, washed with H₂O and dried, yielding 0.44g (88%) of intermediate 9.

References:

WO2007/82878,2007,A1 Location in patent:Page/Page column 28