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

HRID 2191242Notes

Reaction equation

HRID 2191242 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

4

Reactant 3

HCID 7498Benzyl BromideHCID 52888501-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dioneHCID 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.

Workup

  1. custom1-Benzyl-5-(2-(pyridin-3-yl-oxymethyl)-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (21b) was prepared
  2. customthe crude product was purified with ether

Sources & evidence

ORD record
ord-ca79aa74e338480ca280b17cafb74f2f
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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