Triethylamine → 6,7-Dimethyl-4,9-bis[(trimethylsilyl)ethynyl][1,2,5]thiadiazolo[3,4-g]quinoxaline

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Reaction Conditions

Reaction Steps

4,9-Dibromo-6,7-dimethyl[1,2,5]thiadiazolo[3,4-g]quinoxaline (68.0 mg, 1.82×10−4 mol), Pd2dba3 (36.0 mg, 3.93×10−5 mol), AsPh3 (62.2 mg, 2.03×10−4 mol), (trimethylsilyl)acetylene (0.60 ml, 4.2×10−3 mol), Et3N (2.0 ml), and THF (15 ml) were added to a 100-ml Schlenk tube. The reaction mixture was stirred at 45° C. for 18.5 h under N2. After the solvent was evaporated, the residue was chromatographed on silica gel using 8:1 hexanes:THF as the eluant. Yield=0.051 g (69% based on 68.0 mg of 4,9-dibromo-6,7-dimethyl[1,2,5]thiadiazolo[3,4-g]quinoxaline). 1H NMR (360 MHz, CDCl3): δ 2.83 (s, 6H, —CH3), 0.42 (s, 18H, —Si—CH3). Chemical Ionization MS m/z: 408.1264 (M+) (calcd 408.126).

Provenance & Evidence