(S)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione → 5-[2-(pyridin-3-yloxymethyl)pyrrolidin-1-yl]sulfonyl-1H-indole-2,3-dione

HRID 2191240Notes

Reaction equation

HRID 2191240 reaction equation
[O:1]([CH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[S:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[C:20]2=[O:27])(=[O:16])=[O:15])[C:2]1[CH:7]=C[CH:5]=[CH:4][CH:3]=1.C(OC([N:35]1CCCC1COC1C=NC=CC=1)=O)(C)(C)C>>[N:35]1[CH:5]=[CH:4][CH:3]=[C:2]([O:1][CH2:8][CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[S:14]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21](=[O:26])[C:20]3=[O:27])(=[O:15])=[O:16])[CH:7]=1

Participants

3

Reactant 2

HCID 9821545(S)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dioneHCID 218517822-(Pyridin-3-yl-oxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 689306805-[2-(pyridin-3-yloxymethyl)pyrrolidin-1-yl]sulfonyl-1H-indole-2,3-dioneYield 82%

Procedure

5-(2-(Pyridin-3-yl-oxymethyl)-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (20) was prepared according to the same procedure for compound 10, except using compound 19, and the crude product was recrystallized from ethyl acetate to afford 1.75 g (82%) of 20 as a yellow solid, mp 215.9-217.8° C. 1H NMR (300 MHz, DMSO) δ 11.42 (s, 1H), 8.26 (d, J=3.0 Hz, 1H), 8.16 (d, J=4.5 Hz, 1H), 8.02 (d, J=8.4 Hz, 1H), 7.78 (s, 1H), 7.38 (m, 1H), 7.33 (m, 1H), 7.05 (d, J=8.4 Hz, 1H), 4.15-4.02 (m, 2H), 3.90 (m, 1H), 3.34 (m, 1H), 3.12 (m, 1H), 1.87 (m, 2H), 1.67-1.54 (m, 2H). LCMS m/e: 387.8 (M+H). Anal. Calcd for C18H17N3O5S.0.5H2O: C, 54.54, H, 4.58; N, 10.60. Found: C, 54.56, H, 4.70; N, 10.04.

Workup

  1. custom5-(2-(Pyridin-3-yl-oxymethyl)-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (20) was prepared
  2. customthe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ea640046e98f40519e3f4822de13ce69
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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