Bromine → HCID 66958789, compound

HRID 1984398Notes

Reaction equation

HRID 1984398 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]1[N:18]([CH2:19][CH2:20][CH3:21])[N:17]=[C:16]([C:22]#[N:23])[CH:15]=1.C([O-])(=O)C.[K+].[Br:29]Br.S([O-])(O)=O.[Na+]>C(O)(=O)C.ClCCl.O>[Br:29][C:15]1[C:16]([C:22]#[N:23])=[N:17][N:18]([CH2:19][CH2:20][CH3:21])[C:14]=1[CH2:13][CH2:12][N:3]1[C:2](=[O:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:11]

Participants

8

Reactant 4

HCID 24408BromineHCID 517044Potassium AcetateHCID 23665763Sodium BisulfiteHCID 66958558HCID 66958558, compound

Product 1

HCID 66958789HCID 66958789, compoundYield 97.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1-propyl-1H-pyrazole-3-carbonitrile (14.1 g, 45.7 mmol) and potassium acetate (6.73 g, 68.6 mmol) in acetic acid (91 mL) and dichloromethane (46 mL) was slowly added bromine (3.28 g, 64.0 mmol). The mixture was stirred for one day. Saturated aqueous sodium hydrogensulfite was added until the mixture became colorless, then the mixture was concentrated under reduced pressure to form a slurry. Water (450 mL) was added to the slurry and a white solid was isolated by filtration, washed with water, and dried to afford 17.24 g of 4-bromo-5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1-propyl-1H-pyrazole-3-carbonitrile as a white solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto form a slurry
  3. customa white solid was isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b630fe541f5f4cd6aea62685d4df5339
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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