HCID 67972215, compound → HCID 67972560, compound

Participants

Reaction Steps

To a stirred solution of 0.60 g (1.8 mmol) of the title compound from Step A above in 10 mL of anhydrous tetrahydrofuran cooled to 0° C. under a nitrogen atmosphere was added 3.0 mL (9.0 mmol) of a 3.0 M methyl magnesium bromide solution in tetrahydrofuran. The resulting mixture was allowed to warm to ambient temperature over 8 h then quenched with water. The layers were separated and the aqueous phase extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with a 0-100% ethyl acetate in hexanes gradient to afford the title compound as a yellow gum (0.40 g, 69% yield). (500 MHz, CDCl3) δ 7.56 (td, J=8.1, 1.7 Hz, 1H), 7.21-7.16 (m, 1H), 7.06 (t, J=8.1, 1H), 6.97 (dd, J=12.7, 8.1 Hz, 1H), 3.40-3.38 (m, 4H), 2.45 (br s, 4H), 1.44 (s, 9H), 1.43 (s, 3H), 1.42 (s, 3H). LC-MS: m/z (ES) 323.0 (MH)+.

Provenance & Evidence