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

HRID 2191233Notes

Reaction equation

HRID 2191233 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11]([N:14]3C[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].O(C[C@@H]1CCN1S(C1C=C2C(=CC=1)NC(=O)C2=O)(=O)=O)C1C=CC=CC=1.[CH3:55][S:56][C:57]1[CH:64]=[CH:63][C:60](CBr)=[CH:59][CH:58]=1>>[CH3:55][S:56][C:57]1[CH:64]=[CH:63][C:60]([CH2:1][N:2]2[C:10]3[C:5](=[CH:6][C:7]([S:11]([N:14]4[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:13])=[O:12])=[CH:8][CH:9]=3)[C:4](=[O:27])[C:3]2=[O:28])=[CH:59][CH:58]=1

Participants

4

Reactant 3

HCID 52888501-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dioneHCID 113679304-(Methylthio)benzyl bromideHCID 11624920(S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione

Product 1

HCID 11497112(S)-1-(4-methylthiobenzyl)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dioneYield 45%

Procedure

(S)-1-(4-Methylthiobenzyl)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione (18d) was prepared according to the same procedure for compound 11a, except using compound 17 and 4-methylthiobenzyl bromide, and purified with hexanes-ether (1:2) to afford 57 mg (45%) of 18d as an orange solid, mp 167.6-169.2° C. 1H NMR (300 MHz, CDCl3) δ 8.05 (d, J=1.5 Hz, 1H), 7.96 (dd, J=8.4 Hz, J=1.8 Hz, 1H), 7.25 (m, 6H), 6.95 (t, J=7.2 Hz, 1H), 6.86-6.78 (m, 3H), 4.89 (s, 2H), 4.46 (m, 1H), 4.11 (m, 2H), 3.82 (m, 2H), 2.49 (s, 3H), 2.39-2.25 (m, 2H). Anal. Calcd for C26H24N2O5S2: C, 61.40, H, 4.76; N, 5.51. Found: C, 60.99, H, 4.71; N, 5.36.

Workup

  1. custom(S)-1-(4-Methylthiobenzyl)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione (18d) was prepared
  2. custompurified with hexanes-ether (1:2)

Sources & evidence

ORD record
ord-ff41c1e5c51b4ef1974aae7e9904b9d7
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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