Bromine → HCID 66958959, compound

HRID 2283792Notes

Reaction equation

HRID 2283792 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]([CH3:19])[N:17]=[C:16]([C:20]#[N:21])[CH:15]=1.C([O-])(=O)C.[K+].[Br:27]Br.S([O-])(O)=O.[Na+]>C(O)(=O)C.ClCCl.O>[Br:27][C:15]1[C:16]([C:20]#[N:21])=[N:17][N:18]([CH3:19])[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 66958438HCID 66958438, compound

Product 1

HCID 66958959HCID 66958959, compoundYield 84.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1-methyl-1H-pyrazole-3-carbonitrile (8.50 g, 30.3 mmol) and potassium acetate (4.50 g, 45.5 mmol) in acetic acid (40 mL) and dichloromethane (120 mL) was slowly added bromine (6.79 g, 42.5 mmol). The mixture was stirred overnight. Saturated aqueous sodium hydrogensulfite was added until the mixture became colorless, then the mixture was concentrated under reduced pressure to form a slurry. Water (200 mL) was added to the slurry and a white solid was isolated by filtration, washed with water, and dried to afford 9.15 g of 4-bromo-5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1-methyl-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-c80dae0e4e6a476d948d29fd17d78865
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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