Iodoethane → HCID 22676740, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 3-[3-(cyclopropylmethoxy)phenyl]-5-(2-hydroxyethoxy)-1-(3-methoxybenzyl)-1-H-indole-2-carboxylate (Example 223, 110 mg, 0.23 mmol) was added to a cooled (0° C.) and stirred suspension of sodium hydride (12 mg, 0.50 mmol) in N,N-dimethylformamide (5 mL). The cold bath was removed and the reaction was stirred for 1 h. Ethyl iodide (80 μL, 156 mg, 1.0 mmol) was added and the reaction was stirred for an additional hour. The reaction was quenched with methanol (1 mL) and then diluted with water (50 mL). The product was extracted with ethyl acetate (3×30 mL) and then the combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Flash chromatography of the residue over silica gel using 4:1 hexane/ethyl acetate gave 62 mg (50%) of product. The product had: 1H NMR (300 MHz, acetone-D6) δ 7.42 (d, 1 H), 7.29-7.36 (m, 2 H), 7.14 (dd, 1 H), 6.94-7.02 (m, 4 H), 6.63-6.79 (m, 3 H), 5.78 (s, 2 H), 3.99-4.12 (m, 4 H), 3.86 (d, 2 H), 3.64-3.71 (m, 5 H), 3.48 (q, 2 H), 1.24-1.34 (m, 1 H), 1.11 (t, 3 H), 0.98 (t, 3 H), 0.54-0.64 (m, 2 H), 0.32-0.42 (m, 2 H).

Provenance & Evidence