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

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Reaction Steps

To flask containing AlCl3 (1.57 g, 11.7 mmol) was added a solution of the title compound of Example 3 Step C (1.39 g, 2.94 mmol) in benzene (8.0 mL). After 1 h, the reaction mixture was quenched by addition of sat. aq. NH4Cl. The aqueous phase was extracted with EtOAc, and organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 25%, then 25 to 100% EtOAc in hexanes) provided the title compound: LCMS A, tr=4.03 min, m/z 384.3 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 9.29 (s, 1H), 7.94 (d, J=8.5 Hz, 2H), 7.68 (s, 1H), 7.40-7.28 (m, 4H), 7.07 (d, J=1.5 Hz, 1H), 3.92 (s, 3H), 3.63 (dddd, J=8.0, 8.0, 6.0, 6.0 Hz 1H), 3.22 (dd, J=14.0, 8.5 Hz, 1H), 2.93 (dd, J=14.0 Hz, 6.0 Hz, 1 H), 1.92-1.84 (m, 1H), 1.66-1.59 (m, 1H), 1.41-1.34 (m, 2H), 0.93 (t, J=7.5 Hz, 3H).

Provenance & Evidence