Sodium hydride → Methyl 4-[(2rs)-2-({5-chloro-1-[4-(trifluoromethyl)benzyl]-1h-indol-2-yl}carbonyl)pentyl]benzoate

Participants

Reaction Steps

To a solution of the title compound of Example 3 Step D (39.0 mg, 0.10 mmol) in DMF (1.0 mL) was added NaH (4.3 mg, 60% suspension in mineral oil, 0.11 mmol). After 10 min, a solution of 4-trifluoromethylbenzyl bromide (26.0 mg, 0.11 mmol) in DMF (0.5 mL) was added, and the reaction mixture was stirred for 18 h, whereupon it was quenched by addition of sat. aq. NaHCO3. The aqueous phase was extracted with EtOAc, and the organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 10%, then 10 to 100% EtOAc in hexanes) provided the title compound: LCMS A, tr=4.65 min, m/z 542.1 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.87 (d, J=8.5 Hz, 2H), 7.71 (d, J=1.5 Hz, 1H), 7.51 (d, J=8.5 Hz, 2H), 7.33-7.23 (m, 3H), 7.19 (d, J=8.5 Hz, 2H), 6.98 (d, J=8.0 Hz, 2H), 5.88 (ABq, J=16.5 Hz, Δν=86 Hz, 2H), 3.91 (s, 3H), 3.69 (dddd, J=9.0, 9.0, 5.5, 5.5 Hz, 1H), 3.10 (dd, J=13.5, 9.0 Hz, 1H), 2.85 (dd, J=13.5, 5.5 Hz, 1H), 1.79-1.74 (m, 2H), 1.58-1.53 (m, 2H), 0.92 (t, J=7.0 Hz, 3H).

Provenance & Evidence