[S:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.C([Li])CCC.[CH2:11]([Sn:15]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])Cl)[CH2:12][CH2:13][CH3:14].C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:21]([Sn:15]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:17][CH2:18][CH2:19][CH3:20])[C:5]1[S:1][N:2]=[CH:3][CH:4]=1)[CH2:22][CH2:23][CH3:24]To a cold (−78° C.) solution of isothiazole (100 mg, 1.175 mmol) in anhydrous THF (2.0 mL) was added n-butyllithium (0.808 mL, 1.292 mmol) dropwise. The reaction mixture was stirred for 60 minutes at −78° C. A solution of tributylchlorostannane (0.380 mL, 1.410 mmol) in anhydrous THF (0.5 mL) was added, and the reaction mixture was stirred for 30 minutes at −78° C. The solution was allowed to warm to room temperature over a 1 hour period. Saturated aqueous sodium bicarbonate was added and the aqueous phase was extracted with EtOAc. The combined organic phase was dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel chromatography (Flash 60 column) eluting with hexane/EtOAc (19:1) to give the title compound as a pale yellow oil (139.3 mg, 32%). 1H NMR (500 MHz, CDCl3) δ ppm 0.90 (t, J=7.32 Hz, 9H), 1.14-1.20 (m, 6H), 1.28-1.39 (m, 6H), 1.51-1.62 (m, 6H), 7.27-7.32 (m, 1H), 8.66 (d, J=1.46 Hz, 1H).
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