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

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Reaction Steps

(S)-1-(4-Fluorobenzyl)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione (18e) was prepared according to the same procedure for compound 11a, except using compound 17 and 4-fluorobenzyl bromide, and purified with hexanes-ether (1:2) to afford 85 mg (71%) of 18e as an orange solid, mp 164.6-165.7° C. 1H NMR (300 MHz, CDCl3) δ 8.05 (d, J=1.8 Hz, 1H), 7.97 (dd, J=8.4 Hz, J=2.1 Hz, 1H), 7.34-7.20 (m, 4H), 7.07 (t, J=8.7 Hz, 2H), 6.94 (t, J=7.2 Hz, 1H), 6.86-6.77 (m, 3H), 4.90 (s, 2H), 4.47 (m, 1H), 4.10 (m, 2H), 3.85 (m, 2H), 2.36-2.22 (m, 2H). Anal. Calcd for C25H21FN2O5S: C, 62.49, H, 4.41; N, 5.83. Found: C, 62.27, H, 4.48; N, 5.69.

Provenance & Evidence