m-Chloroperbenzoic acid → HCID 178526239, compound

HRID 244644Notes

Reaction equation

HRID 244644 reaction equation
[CH:1]1([C:4]2[NH:12][C:7]3=[N:8][CH:9]=[CH:10][CH:11]=[C:6]3[CH:5]=2)[CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:18].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>COCCOC>[CH:1]1([C:4]2[NH:12][C:7]3=[N+:8]([O-:18])[CH:9]=[CH:10][CH:11]=[C:6]3[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 497590992-Cyclopropyl-1H-pyrrolo[2,3-B]pyridine

Product 1

HCID 178526239HCID 178526239, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 2-cyclopropyl-1H-pyrrolo[2,3-b]pyridine (7.6 g) in DME (100 ml) was added a solution of m-chloroperoxybenzoic acid (17.9 g) in DME (50 ml), under an atmosphere of nitrogen, keeping the temperature between 20 and 25° C. The resulting suspension was stirred at 20° C. for 45 min and then sodium metabisulphite solution (20 ml, 40%) was added. The mixture was concentrated in vacuo to ˜80 ml. Water (100 ml) was added and the mixture basified by the addition of aqueous potassium carbonate solution. The suspension was stirred for 14 h and then the precipitate was collected by filtration, washed with water and dried to give the title compound (4.1 g).

Workup

  1. customthe temperature between 20 and 25° C
  2. concentrationThe mixture was concentrated in vacuo to ˜80 ml
  3. additionWater (100 ml) was added
  4. additionthe mixture basified by the addition of aqueous potassium carbonate solution
  5. stirringThe suspension was stirred for 14 h
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-e8d5199ef5ca46c282a2938f22963e79
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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