(S)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione → 5-[2-(pyridin-4-yloxymethyl)pyrrolidin-1-yl]sulfonyl-1H-indole-2,3-dione

HRID 2191244Notes

Reaction equation

HRID 2191244 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]=[CH:6]C=[CH:4][CH:3]=1.C(OC([N:35]1CCCC1COC1C=CN=CC=1)=O)(C)(C)C>>[N:35]1[CH:6]=[CH:7][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:3][CH:4]=1

Participants

3

Reactant 2

HCID 9821545(S)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dioneHCID 689337972-(Pyridin-4-yl-oxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 689297845-[2-(pyridin-4-yloxymethyl)pyrrolidin-1-yl]sulfonyl-1H-indole-2,3-dioneYield 55%

Procedure

5-(2-(Pyridin-4-yl-oxymethyl)-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (23) was prepared according to the same procedure for compound 10, except using compound 22, purified with ethyl acetate to afford 1.17 g (55%) of 23 as a yellow solid, mp 204.2-205.3° C. 1H NMR (300 MHz, CDCl3) δ 11.44 (s, 1H), 8.37 (d, J=5.7 Hz, 2H), 8.03 (dd, J=8.4 Hz, J=2.1 Hz, 1H), 7.79 (s, 1H), 7.06 (d, J=8.4 Hz, 1H), 6.96 (d, J=6.0 Hz, 2H), 4.17-4.05 (m, 2H), 3.90 (m, 1H), 3.32 (m, 1H), 3.10 (m, 1H), 1.85 (m, 2H), 1.60 (m, 2H). LCMSm/e: 387.9 (M+H). Anal. Calcd for C18H17N3O5S.0.75H2O: C, 53.92, H, 4.65; N, 10.48. Found: C, 54.14, H, 4.39; N, 10.35.

Workup

  1. custom5-(2-(Pyridin-4-yl-oxymethyl)-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (23) was prepared
  2. custompurified with ethyl acetate

Sources & evidence

ORD record
ord-3b3a7ec4ca22433bad0e8c60d5c054ad
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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