Trimethylsilyl iodide → N1-[5-(2-Fluoro-4-trifluoromethylphenyl)oxazol-2-yl]-5,6,7,8-tetrahydronaphthalene-1,7-diamine

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Reaction Steps

Iodotrimethylsilane (52 mg, 0.260 mmol) was added dropwise to a solution of the product of Example 22B (107 mg, 0.218 mmol) in 1 mL CH2Cl2 at ambient temperature. After 15 minutes the reaction was diluted with CH2Cl2 and quenched with 1N aq NaOH solution. The mixture was stirred 15 minutes and then poured into water. The separated organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was triturated with Et2O/hexanes and the solid collected by vacuum filtration and dried under high vacuum. The result was 36 mg (42%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 9.42 (br s, 1H), 7.75 (m, 3H), 7.52 (d, J=8.1 Hz, 1H), 7.44 (d, J=3.7 Hz, 1H), 7.11 (t, J=7.5 Hz, 1H), 6.88 (d, J=7.5 Hz, 1H), 3.05-2.70 (m, 4H), 2.30 (m, 1H), 1.86 (m, 1H), 1.70 (br s, 2H), 1.43 (m, 1H); MS (ESI+) m/z 392 (M+H)+.

Provenance & Evidence