1-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione → HCID 11525874, compound

HRID 2191238Notes

Reaction equation

HRID 2191238 reaction equation
CN1C2C(=CC(S(N3CCC[C@H]3COC3C=CC=CC=3)(=O)=O)=CC=2)C(=O)C1=O.[O:29]([CH2:36][C@@H:37]1[CH2:40][CH2:39][N:38]1[S:41]([C:44]1[CH:45]=[C:46]2[C:50](=[CH:51][CH:52]=1)[NH:49][C:48](=[O:53])[C:47]2=[O:54])(=[O:43])=[O:42])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Br[CH2:56][C:57]1[N:62]=[C:61]([F:63])[CH:60]=[CH:59][CH:58]=1>>[F:63][C:61]1[N:62]=[C:57]([CH2:56][N:49]2[C:50]3[C:46](=[CH:45][C:44]([S:41]([N:38]4[CH2:39][CH2:40][C@H:37]4[CH2:36][O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)(=[O:43])=[O:42])=[CH:52][CH:51]=3)[C:47](=[O:54])[C:48]2=[O:53])[CH:58]=[CH:59][CH:60]=1

Participants

4

Reactant 3

HCID 52888501-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dioneHCID 11624920(S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dioneHCID 139852182-(Bromomethyl)-6-fluoropyridine

Product 1

HCID 11525874HCID 11525874, compoundYield 52%

Procedure

(S)-1-(6-Fluoropyridin-2-yl-methyl)-5-(2-phenoxymethylazetidine-1-sulfonyl)-1H-indole-2,3-dione (18i) was prepared according to the same procedure for compound 11a, except using compound 17 and 6-(bromomethyl)-2-fluoropyridine, and purified with ether to afford 62 mg (52%) of 18i as an orange solid, mp 144.7-146.1° C. 1H NMR (300 MHz, CDCl3) δ 8.03 (s, 1H), 8.00 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.82 (m, 1H), 7.27-7.11 (m, 4H), 6.92 (m, 2H), 6.79 (m, 2H). Anal. Calcd for C24H20FN3O5S: C, 59.87, H, 4.19; N, 8.73. Found: C, 59.59, H, 4.27; N, 8.48.

Workup

  1. custom(S)-1-(6-Fluoropyridin-2-yl-methyl)-5-(2-phenoxymethylazetidine-1-sulfonyl)-1H-indole-2,3-dione (18i) was prepared
  2. custompurified with ether

Sources & evidence

ORD record
ord-83a831c5e7d843c890c1d5c31b80b0f2
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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