Potassium Cyanide → HCID 14882502, compound

Reaction equation

Cl[CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][CH:4]=1.[C-:22]#[N:23].[K+].O1CCOCCOCCOCCOCCOCC1>C(#N)C>[CH3:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[C:3]([CH2:2][C:22]#[N:23])[CH:11]=3)[CH:7]=[CH:8]2)(=[O:13])=[O:14])=[CH:20][CH:19]=1

Participants

Procedure

A solution of 6-chloromethyl-1-(4-methylphenylsulfonyl)indole (21.5 g) in acetonitrile (224 ml) was treated with potassium cyanide (8.8 g) and 1,4,7,10,13,16-hexaoxacyclooctadecane (3.6 g) and stirred at room temperature under a nitrogen atmosphere for 18 hr. The solution was poured onto ice and extracted with methylene chloride. The organic phase was washed with water and brine, dried (MgSO4) and evaporated. The resultant amber oil was purified by flash chromatography, eluting with 1:5 ethyl acetate:hexane, to give 1-(4-methylphenylsulfonyl)indole-6-acetonitrile (14.4 g, 76%) as a white powder; partial NMR (80 MHz, CDCl3): 2.34(s, 3H, ArCH3), 3.84(s, 2H, NCCH2), 6.62(dd, 1H, H3 -indole), 7.94(m, 1H, H7 -indole)