Chlorosuccinimide → HCID 19823240, compound

HRID 728045Notes

Reaction equation

HRID 728045 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][CH:20]3[CH2:24][CH2:23][N:22]([CH3:25])[C:21]3=[O:26])=[CH:16][CH:17]=2)[C:12]([CH2:27][C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][C:29]=2[O:38][CH3:39])=[CH:11]1>ClCCl>[Cl:1][C:11]1[N:10]([CH3:9])[C:18]2[C:13]([C:12]=1[CH2:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][C:29]=1[O:38][CH3:39])=[CH:14][C:15]([CH2:19][CH:20]1[CH2:24][CH2:23][N:22]([CH3:25])[C:21]1=[O:26])=[CH:16][CH:17]=2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 17943769HCID 17943769, compound

Product 1

HCID 19823240HCID 19823240, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Chlorosuccinimide (0.282 mg) was added in one portion to a stirred solution of methyl 4-[1-methyl -5-(1-methyl-2-oxopyrrolidin-3-ylmethyl)indol-3-ylmethyl]-3-methoxybenzoate (0.9 g) in dry dichloromethane (20 ml), under a nitrogen atmosphere. After 15 minutes, the solvent was evaporated, and the product was purified by flash chromatography, eluting with ethyl acetate, to give methyl 4-[2-chloro-1-methyl-5-(1-methyl-2-oxopyrrolidin -3-ylmethyl)indol-3-ylmethyl](65%) as a yellow oil: NMR (300 MHz, DMSO-d6): 1.45-1.61 (m, lH), 1.75-1.90 (m, lH), 2.50-2.70 (m, 5H), 2.90-3.18 (m, 3H), 3.72 (s, 3H, CH3), 3.82 (s, 3H, CH3), 3.92 (s, 3H, CH3), 4.02 (s, 2H), 6.99-7.10 (m, 2H), 7.20 (s, 1), 7.38 (d, lH), 7.40-7.50 (m, 2H).

Workup

  1. customthe solvent was evaporated
  2. customthe product was purified by flash chromatography
  3. washeluting with ethyl acetate
  4. customto give methyl 4-[2-chloro-1-methyl-5-(1-methyl-2-oxopyrrolidin -3-ylmethyl)indol-3-ylmethyl](65%) as a yellow oil

Sources & evidence

ORD record
ord-bba9d80a25504d84bf913c18c29e6622
Source dataset
uspto-grants-1991_09
Patent number
US05047402

Reaction notes

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