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

Participants

Reaction Steps

To a cooled (−78° C.) solution of the title compound of Example 3 Step B (1.50 g, 4.61 mmol) in THF (20 mL) was added KHMDS (13.8 mL, 0.5 M in toluene, 6.90 mmol). After 25 min, a solution of methyl 4-bromomethyl benzoate (1.27 g, 5.54 mmol) in THF (5 mL) was added, and the resultant mixture was allowed to warm slowly to room temperature over 4 h. The reaction mixture was then poured into sat. aq. NH4Cl, and the aqueous phase was extracted with EtOAc. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo: LCMS A, tr=4.52 min, m/z 474.2 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.84 (d, J=8.0 Hz, 2 h), 7.64-7.63 (m, 1H), 7.27-7.25 (m, 3H), 7.22-7.19 (m, 2H), 7.15 (d, J=8.0 Hz, 2H), 7.14 (s, 1H), 5.80 (ABq, J=16.0 Hz, Δν=61.8 Hz, 2H), 3.87 (s, 3H), 3.63-3.59 (m, 1H), 3.07 (dd, J=13.5, 8.5 Hz, 1H), 2.77 (dd, J=13.5, 6.0 Hz, 1H), 1.74-1.69 (m, 1H), 1.53-1.45 (m, 1H), 1.23-1.18 (m, 2H), 0.82 (t, J=7.5 Hz, 3H).

Provenance & Evidence