Reaction SMILES: [Br:1][C:2]1[CH:3]=[C:4]([C@H:8]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:14]=[CH:13]2)[CH2:9][CH2:10]O)[CH:5]=[CH:6][CH:7]=1.[N:29]1C(C)=CC=[CH:31][C:30]=1C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[Li]CC#N>ClCCl.O1CCCC1>[CH2:22]([O:21][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[N:12]([C@@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH2:9][CH2:10][CH2:31][C:30]#[N:29])[CH:13]=[CH:14]2)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
Reactant: OCC[C@H](c1cccc(Br)c1)n1ccc2cccc(OCc3ccccc3)c21
Reactant: Cc1cccc(C)n1
Agent: O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F
Agent: [Li]CC#N
Solvent: ClCCl
Solvent: C1CCOC1
Product: N#CCCC[C@H](c1cccc(Br)c1)n1ccc2cccc(OCc3ccccc3)c21
Reaction time: 0.33 h
Yield: 78.1 %

Procedure:
A solution of (3R)-(-)-3-(3-bromophenyl)-3-(7-benzyloxyindol-1-yl)propan-1-ol (5.10 g, 11.62 mmol) and 2,6-lutidine (1.24 g, 11.62 mmol) in dry dichloromethane (20.0 ml) was added dropwise to a magnetically stirred solution of trifluoromethanesulfonic anhydride (2.20 ml, 13.10 mmol) in dichloromethane (40.0 ml) at -10° C. under nitrogen over a 25 min. period. The resulting grey solution was stirred below -10° C. for 20 min., quenched with water (250 ml), extracted into dichloromethane (2×200 ml), the combined organic extracts were washed with water (200 ml), dried (Na2SO4) and the solvent removed in vacuo at room temperature to give an orange/brown oil which was dissolved in dry tetrahydrofuran (40.0 ml) and added dropwise to the stirred lithio acetonitrile reagent (52.19 mmol) in tetrahydrofuran at -70° C. TLC inspection immediately after the addition showed that the reaction was complete. Quenched with water (20.0 ml), diluted with ethyl acetate (300 ml), washed with brine (2×200 ml), dried (Na2SO4) and adsorbed onto silica (ca. 12.0 g). Column chromatography (ethyl acetate--light petroleum (b.p. 40-60° C.), 1.4) gave the title compound as a pale yellow oil (4.17 g, 78%). (Found: C, 67.62; H, 5.04; N 5.94; Br, 17.60. C26H23BrN2O requires C, 67.98; H, 5.05; N, 6.10; Br, 17.39%); -[α]D19 -138 (c=0.010 gml-1, CHCl3); Vmax (thin film)/cm-1 3064, 2934, 2871, 2246.5 (CN), 1575; δH (270 MHz) 1.55 (2H, m, 2×butyl 3-H); 2.23 (2H, t, 2×butyl 4-H, 3J4.3 =6.9 Hz); 2.30 (2H, m, 2×butyl 2-H); 5.17 (2H, q, CH2Ph, 2J=10.9 Hz); 6.35 (1H, dd, butyl 1-H, 3J1.2 =9.7, J1.2' =5.8 Hz); 6.56 (1H, d, 3-H, 3J3.2 =3.3 Hz); 6.74 (1H, d, 6-H, Jo =7.9 Hz); 6.95 (1H, d, 4-H, Jo =7.9 Hz); 7.00 (1H, t, 5-H, Jo =7.9 Hz); 7.08 (1H, t, 5'-H, Jo =7.9 Hz); 7.14 (1H, d, 2-H, 3J3.2 3.3 Hz); 7.21 (1H, d, 6'H, Jo =8.9 Hz); 7.25 (1H, t, 2'-H, Ja =1.1 Hz); 7.34 (1H, dd, 4'-H, Jo =8.4, Ja =1.5 Hz); 7.42 (5H, m 5ArH). δc (67.8 MHz) 16.5 (butyl 3-C); 22.3 (butyl 4-C); 34.4 (butyl 2-C); 58.8 (butyl 1-C); 70.6 (PhCH2); 103.5 (indole 3-C); 104.1 (indole 6-C); 114.2 (indole 4-C); 119.1 (CN); 120.2 (indole 5-C); 122.6 (3'-C); 124.5 (indole 2-C); 125.0 (6'-C); 130.7 (1'-C); 136.5 (benzyl ipso-C); 144.2 (indole 7a-C); 147.0 (indole 7-C). The remaining signals lie between 128.2-130.6 ppm and cannot be assigned with any certainty; m/z 460.1, 458.1 (3.43, 3.32), 369.1, 367.1 (1.79, 1.66); 239.0, 237.0 (7.01, 7.72), 171.0, 169.0 (26.03, 26.07), 143.1 (100), 132.1 (6.44), 116.0 (9.37).