Chlorosuccinimide → HCID 59304982, compound

HRID 2240212Notes

Reaction equation

HRID 2240212 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[NH:19][C:20]1[C:21]2[CH:28]=[CH:27][NH:26][C:22]=2[N:23]=[CH:24][CH:25]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:1][C:28]1[C:21]2[C:20]([NH:19][C:11]3[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:10]=3[F:9])=[CH:25][CH:24]=[N:23][C:22]=2[NH:26][CH:27]=1

Participants

5

Reactant 3

HCID 31398Chlorosuccinimide2×HCID 516892Sodium BicarbonateHCID 59304985HCID 59304985, compound

Product 1

HCID 59304982HCID 59304982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

108 mg (810 μmol) of N-chlorosuccinimide are added to a solution of 200 mg (730 μmol) of N-(2-fluoro-4-nitrophenyl)-1H-pyrrolo[2,3-b]pyridine-4-amine in 5 ml of THF, and the mixture is stirred at RT overnight. To bring the reaction to completion, another 49 mg (365 μmol) of N-chlorosuccinimide are added, and the mixture is stirred for another night. Saturated sodium bicarbonate solution is then added to the reaction mixture, and the mixture is extracted with ethyl acetate. The organic phases are washed with saturated sodium chloride solution and then dried with magnesium sulfate, and the solvent is removed under reduced pressure. Purification by column chromatography on silica gel (mobile phase: gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate 100%) and preparative RP-HPLC affords the title compound.

Workup

  1. customthe reaction to completion
  2. stirringthe mixture is stirred for another night
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic phases are washed with saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customPurification by column chromatography on silica gel (mobile phase: gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate 100%) and preparative RP-HPLC

Sources & evidence

ORD record
ord-953800258eae4df6850a891994ee5956
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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