4-Fluorobenzyl bromide → (S)-1-(4-fluorobenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione

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Reaction Steps

(S)-1-(4-Fluorobenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (11c) was prepared according to the same procedure for compound 11a, except using 4-fluorobenzyl bromide, and purified with hexanes-ether (1:2) to afford 196 mg (79%) of 11c as an orange solid, mp 74.5-75.4° C. 1H NMR (300 MHz, CDCl3) δ 7.99 (s, 1H), 7.95 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.34-7.19 (m, 4H), 7.06 (t, J=8.7 Hz, 2H), 6.92 (t, J=7.2 Hz, 1H), 6.87-6.79 (m, 3H), 4.89 (s, 2H), 4.13 (m, 1H), 3.93 (m, 2H), 3.47 (m, 1H), 3.23 (m, 1H), 2.01 (m, 2H), 1.78 (m, 2H). Anal. Calcd for C26H23FN2O5S: C, 63.15, H, 4.69; N, 5.66. Found: C, 63.05, H, 4.69; N, 5.60.

Provenance & Evidence