Chlorosuccinimide → HCID 67464076, compound

HRID 42526Notes

Reaction equation

HRID 42526 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]2[CH:6]=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[Cl:18]N1C(=O)CCC1=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]2[C:6]([Cl:18])=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 67466539methyl 6-bromo-1-isopropyl-1H-indole-4-carboxylate

Product 1

HCID 67464076HCID 67464076, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 100 ml round bottom flask was added methyl 6-bromo-1-(1-methylethyl)-1H-indole-4-carboxylate (1.100 g, 3.71 mmol) as a solution in THF and a magnetic stir bar. To the same was added 1-chloro-2,5-pyrrolidinedione (0.546 g, 4.09 mmol) and the system stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue dissolved in EtOAc (60 ml) and washed with saturated NaHCO3 (20 ml) and brine (8 ml). The organic layer was dried over Na2SO4, filtered and concentrated. Purification of the residue by column chromatography provided methyl 6-bromo-3-chloro-1-isopropyl-1H-indole-4-carboxylate (as a thick gold oil), which was used in the next step. 1H NMR (400 MHz, DMSO-d6) δ 8.15 (d, J=1.52 Hz, 1H), 7.93 (s, 1H), 7.50 (d, J=1.77 Hz, 1H), 4.90 (quin, J=6.63 Hz, 1H), 3.89 (s, 3H), 1.43 (d, J=6.57 Hz, 6H). MS (ES) [M+H]+ 332.2.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in EtOAc (60 ml)
  3. washwashed with saturated NaHCO3 (20 ml) and brine (8 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by column chromatography

Sources & evidence

ORD record
ord-668da48997834d808c330e1069ce5bd1
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Reaction notes

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