C(OC(=O)[NH:7][C:8]1[C:9]([C:14]#[C:15][Si](C)(C)C)=[N:10][CH:11]=[CH:12][CH:13]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)C>[NH:7]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:14]=[CH:15]1A mixture of (2-trimethylsilanylethynylpyridin-3-yl)carbamic acid tert-butyl ester (500 mg, 1.72 mmol) in 5 mL of THF was treated with TBAF (1 M in THF, 10.3 mL) at room temperature. The mixture was heated at reflux for 8 hours, cooled to room temperature, diluted with 100 mL of diethyl ether, and quenched with 100 mL of water. The aqueous layer was extracted with three 50 mL portions of diethyl ether, and the combined organic layers were washed with 500 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography on SiO2 (100% CH2Cl2 to 10% MeOH in CH2Cl2, gradient) gave 160 mg of the title product as tan solid (79% yield).
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