m-Chloroperbenzoic acid → HCID 59457615, compound

HRID 1710687Notes

Reaction equation

HRID 1710687 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5]([NH:14][C:15]([CH:17]2[CH2:19][CH2:18]2)=[O:16])=[N:6][C:7]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.C1C=C(Cl)C=C(C(OO)=[O:28])C=1>C(Cl)Cl>[Br:1][C:2]1[N:3]=[CH:4][C:5]([NH:14][C:15]([CH:17]2[CH2:18][CH2:19]2)=[O:16])=[N:6][C:7]=1[C:8]1[CH:9]=[N+:10]([O-:28])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59457544HCID 59457544, compound

Product 1

HCID 59457615HCID 59457615, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of N-(5-bromo-6-pyridin-3-ylpyrazin-2-yl)cyclopropanecarboxamide (4.02 g, 12.6 mmol) in CH2Cl2 (45 mL), cooled at 0° C., was added mCPBA (3.11 g, 12.6 mmol) in small portions. Upon addition completion the ice bath was removed and the reaction continued at room temperature for 4 h. The mixture was diluted with CH2Cl2 (30 mL) and washed with saturated NaHCO3 (1×25 mL) and saturated NaCl (1×25 mL). The organic layer was concentrated in vaccuo up to 25 mL volume, and the precipitated product was filtered and washed with Et2O (4×5 mL), giving the title compound as a white powder (3.03 g, 72% yield).

Workup

  1. customwas removed
  2. additionThe mixture was diluted with CH2Cl2 (30 mL)
  3. washwashed with saturated NaHCO3 (1×25 mL) and saturated NaCl (1×25 mL)
  4. concentrationThe organic layer was concentrated in vaccuo up to 25 mL volume
  5. filtrationthe precipitated product was filtered
  6. washwashed with Et2O (4×5 mL)

Sources & evidence

ORD record
ord-d60ce7f4aa1842a48d769f33a7820026
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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