Chlorosuccinimide → HCID 57934543, compound

HRID 1950095Notes

Reaction equation

HRID 1950095 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[C:12]1[N:13]([CH3:23])[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([O:21][CH3:22])[CH:15]=2)[CH3:2].[Cl:26]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:26][C:20]1[C:19]2[C:14](=[CH:15][C:16]([O:21][CH3:22])=[CH:17][CH:18]=2)[N:13]([CH3:23])[C:12]=1[C:5]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:4]=1[N:3]([CH2:1][CH3:2])[CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 23087195HCID 23087195, compound

Product 1

HCID 57934543HCID 57934543, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl[5-methoxy-2-(6-methoxy-1-methyl-1H-indol-2-yl)phenyl]amine (110 mg) in tetrahydrofuran (5 ml) was added N-chlorosuccinimide (50 mg), and the solution was stirred for 1 hour at room temperature. To the reaction solution was added a saturated aqueous solution of sodium bicarbonate, the solution was extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate-methanol system) to provide the title compound (96 mg).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-e3d2aabcdfe64dbbaeed7ddb9d2c0f36
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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