Reaction #312619

Reaction equation

(1H-indol-5-yl)-(4-isopropyl-piperazin-1-yl)-methanone

intermediate 1

(1H-indol-5-yl)-(4-isopropyl-piperazin-1-yl)-methanone

toluene

→

title compound

(1-Cyclopentylmethyl-1H-indol-5-yl)-(4-isopropyl-piperazin-1-yl)-methanone

Conditions

Workup

1. 1
   OtherAfter evaporation the residue
2. 2
   Otherwas purified by preparative HPLC on reversed phase
3. 3
   Washeluting with a gradient
4. 4
   Otherformed from acetonitrile/water/NEt3
5. 5
   OtherThe combined product fractions were evaporated

Procedure

A mixture of 21.7 mg (0.08 mmol) (1H-indol-5-yl)-(4-isopropyl-piperazin-1-yl)-methanone (intermediate 1), 16 mg (0.16 mmol) cyclopentylmethynol (commercially available), 38.6 mg (0.16 mmol) cyanomethylenetri-n-butylphospborane in toluene was heated to 110° C. for an extended period of time. After evaporation the residue was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/NEt3. The combined product fractions were evaporated to yield 5.4 mg of the title compound. MS (m/e): 354.4 (MH+).

Source