Benzyl Bromide → 1-Benzyl-5-[2-(pyridin-3-yloxymethyl)pyrrolidin-1-yl]sulfonylindole-2,3-dione

Reaction equation

CN1[C:10]2[C:5](=[CH:6][C:7](S(N3CCC[C@H]3COC3C=CC=CC=3)(=O)=O)=[CH:8][CH:9]=2)[C:4](=O)C1=O.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][CH:37]2[CH2:41][CH2:40][CH2:39][N:38]2[S:42]([C:45]2[CH:46]=[C:47]3[C:51](=[CH:52][CH:53]=2)[NH:50][C:49](=[O:54])[C:48]3=[O:55])(=[O:44])=[O:43])[CH:30]=1.C(Br)C1C=CC=CC=1>>[CH2:4]([N:50]1[C:51]2[C:47](=[CH:46][C:45]([S:42]([N:38]3[CH2:39][CH2:40][CH2:41][CH:37]3[CH2:36][O:35][C:31]3[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=3)(=[O:44])=[O:43])=[CH:53][CH:52]=2)[C:48](=[O:55])[C:49]1=[O:54])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

Reactant 3

HCID 7498Benzyl Bromide

HCID 52888501-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione

HCID 689306805-[2-(pyridin-3-yloxymethyl)pyrrolidin-1-yl]sulfonyl-1H-indole-2,3-dione

Product 1

HCID 689362081-Benzyl-5-[2-(pyridin-3-yloxymethyl)pyrrolidin-1-yl]sulfonylindole-2,3-dioneYield 51%

Procedure

1-Benzyl-5-(2-(pyridin-3-yl-oxymethyl)-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (21b) was prepared according to the same procedure for compound 11a, except using compound 20 and benzyl bromide, and the crude product was purified with ether to afford 61 mg (51%) of 21b as a yellow solid, mp 79.6-80.7° C. 1H NMR (300 MHz, CDCl3) δ 8.25 (s, 1H), 8.22 (t, J=2.7 Hz, 1H), 8.04 (d, J=2.1 Hz, 1H), 7.98 (dd, J=8.4 Hz, J=2.1 Hz, 1H), 7.36 (m, 5H), 7.22 (m, 2H), 6.91 (d, J=8.8 Hz, 1H), 4.97 (s, 2H), 4.25 (m, 1H), 3.99-3.94 (m, 2H), 3.55-3.48 (m, 1H), 3.21-3.15 (m, 1H), 2.10-1.97 (m, 2H), 1.84-1.75 (m, 2H). LRMS (FAB) m/e: 484.1 (M+Li, 100); HRMS (FAB) m/e calcd for C25H23N3O5SLi (M+Li) 484.1518, found 484.1539.