Dichloromethane → HCID 178440579, compound

HRID 244680Notes

Reaction equation

HRID 244680 reaction equation
[CH3:1][C:2]([C:5]1[NH:13][C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)([CH3:4])[CH3:3].C(Cl)Cl.ClC1C=CC=C(C(OO)=[O:25])C=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH3:4][C:2]([C:5]1[NH:13][C:8]2=[N+:9]([O-:25])[CH:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 14849672-tert-butyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 178440579HCID 178440579, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(1,1-Dimethylethyl)-1H-pyrrolo[2,3-b]pyridine (10 g, 57 mmol) was dissolved in ethyl acetate:DCM (400 ml, 1:1, v/v), cooled to ˜0° C. in an ice bath and treated by dropwise addition of m-chloroperbenzoic acid (15.85 g, 69.5 mmol). The reaction was warmed to room temperature over 3 hours then treated with 30% potassium carbonate (aq) (150 ml). The organic layer was separated and the aqueous washed with further DCM (2×100 ml). The combined organic layers were washed with a sodium metabisulphite solution, dried then evaporated to give title compound, 11.1 g.

Workup

  1. customThe organic layer was separated
  2. washthe aqueous washed with further DCM (2×100 ml)
  3. washThe combined organic layers were washed with a sodium metabisulphite solution
  4. customdried
  5. customthen evaporated

Sources & evidence

ORD record
ord-6501af83e37e4900b0071a39333a6bb9
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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