1-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione → (S)-1-(4-methylthiobenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione

HRID 2191228Notes

Reaction equation

HRID 2191228 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11]([N:14]3[CH2:18][CH2:17][CH2:16][C@H:15]3[CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:13])=[O:12])=[CH:8][CH:9]=2)[C:4](=[O:27])[C:3]1=[O:28].[CH3:29][S:30][C:31]1[CH:38]=[CH:37][C:34](CBr)=[CH:33][CH:32]=1>>[CH3:29][S:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:1][N:2]2[C:10]3[C:5](=[CH:6][C:7]([S:11]([N:14]4[CH2:18][CH2:17][CH2:16][C@H:15]4[CH2:19][O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:12])=[O:13])=[CH:8][CH:9]=3)[C:4](=[O:27])[C:3]2=[O:28])=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 52888501-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dioneHCID 113679304-(Methylthio)benzyl bromide

Product 1

HCID 11519268(S)-1-(4-methylthiobenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dioneYield 64%

Procedure

(S)-1-(4-Methylthiobenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (11d) was prepared according to the same procedure for compound 11a, except using 4-methylthiobenzyl bromide, and purified with hexanesether (1:2) to afford 152 mg (64%) of 11d as a yellow solid, mp 175.4-176.8° C. 1H NMR (300 MHz, CDCl3) δ 8.05 (s, 1H), 7.99 (d, J=10.5 Hz, 1H), 7.27 (m, 6H), 6.96 (t, J=7.2 Hz, 1H), 6.86 (t, J=8.1 Hz, 3H), 4.90 (s, 2H), 4.19 (d, J=8.7 Hz, 1H), 3.96 (m, 2H), 3.53 (m, 1H), 3.25 (m, 1H), 2.50 (s, 3H), 2.05 (m, 2H), 1.82 (m, 2H). Anal. Calcd for C27H26N2O5S2: C, 62.05, H, 5.01; N, 5.36. Found: C, 61.81, H, 4.95; N, 5.34.

Workup

  1. custom(S)-1-(4-Methylthiobenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (11d) was prepared
  2. custompurified with hexanesether (1:2)

Sources & evidence

ORD record
ord-0d3cf870e8fc496dab3d89476110ef82
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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