HCID 86644567, compound → HCID 86644566, compound

Participants

Reaction Steps

To a degassed solution of the title compound from Example 7 Step E (115 mg, 0.17 mmol) in EtOAc (5 mL) was added platinum oxide (22 mg). The reaction flask was fitted with a hydrogen balloon attached to a 3-way adapter. The reaction mixture was then evacuated and back-filled with hydrogen. After this process was repeated three times, the reaction mixture was placed under a hydrogen atmosphere, and was stirred vigorously. After 45 min, the reaction mixture was filtered though Celite, rinsing with EtOAc. The mixture was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by chromatography on silica gel (0 to 30% EtOAc in hexanes, 30 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 701.0 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.15 (s, 1H), 8.12 (d, J=8.0 Hz, 1H), 8.01-7.92 (m, 2H), 7.68 (dd, J=8.0, 6.0 Hz, 2H), 7.39 (t, J=8.0 Hz, 1H), 7.15 (dd, J=12.5, 8.5 Hz, 4H), 6.94 (t, 2JH-F=55.5 Hz, 1H), 4.57 (s, 2H), 4.40 (q, J=7.0 Hz, 2H), 4.34-4.16 (br m, 2H), 2.90-2.72 (br m, 2H), 2.68-2.60 (m, 1H), 1.86-1.74 (m, 2H), 1.66-1.56 (m, 2H), 1.49 (s, 9H), 1.40 (t, J=7.0 Hz, 1H).

Provenance & Evidence