[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:15]=[C:14]([CH2:16][CH3:17])[C:11]([C:12]#[N:13])=[C:10]([CH2:18][CH3:19])[CH:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH2:18][CH3:19])[C:11]([CH2:12][NH2:13])=[C:14]([CH2:16][CH3:17])[CH:15]=1Under an inert atmosphere, lithium aluminum hydride (359 mg, 9.4 mmol) was suspended in anhydrous THF (9 mL) was cooled to 0° C. and then a solution of 4-bromo-2,6-diethylbenzonitrile (1.73 g, 7.36 mmol) in anhydrous THF (3 mL) was added dropwise. The reaction mixture was then allowed to warm to ambient temperature and stirring was continued for 20 h. Sodium sulfate decahydrate (6 g) was then added to quench the reaction and the resultant reaction mixture was filtered then the filtrate was then evaporated under reduced pressure. The resultant oil was purified by flash chromatography (silica, 50 g column, ISCO, 0-10% methanol in DCM) to afford the title compound as an orange oil (96 mg, 5%). 1H NMR (DMSO-D6, 400 MHz): 7.18 (s, 2H), 3.68 (s, 2H), 2.73-2.64 (m, 4H), 2.52-2.48 (m, 2H), 1.19-1.11 (m, 6H).
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