Bromine → HCID 66958697, compound

HRID 1984519Notes

Reaction equation

HRID 1984519 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][C:13]1[N:17]([CH3:18])[N:16]=[C:15]([C:19]#[N:20])[CH:14]=1.[Br:21]Br.C([O-])(=O)C.[K+].S([O-])(O)(=O)=O.[Na+]>>[Br:21][C:14]1[C:15]([C:19]#[N:20])=[N:16][N:17]([CH3:18])[C:13]=1[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

5

Reactant 4

HCID 24408Bromine2×HCID 516919Sodium BisulfateHCID 517044Potassium AcetateHCID 66958618HCID 66958618, compound

Product 1

HCID 66958697HCID 66958697, compound

Procedure

5-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1-methyl-1H-pyrazole-3-carbonitrile (1.57 g, 5.90 mmol) was brominated using a modified version of the method described in Part F of Examples 1-4. In the reaction, 1.4 equivalents of bromine were used instead of 1.1 equivalents. After the reaction was stirred for two days, additional potassium acetate (1.31 g) and bromine (0.211 mL) were added, and the reaction was stirred for five more days. After the addition of sodium hydrogensulfate, most of the acetic acid was removed under reduced pressure, and 2 M aqueous sodium carbonate was added. A solid formed and was isolated by filtration, washed with water, and dried on the vacuum filter funnel to provide 1.85 g of 4-bromo-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1-methyl-1H-pyrazole-3-carbonitrile as a white solid.

Workup

  1. stirringthe reaction was stirred for five more days
  2. custommost of the acetic acid was removed under reduced pressure, and 2 M aqueous sodium carbonate
  3. additionwas added
  4. customA solid formed
  5. customwas isolated by filtration
  6. washwashed with water
  7. customdried on the vacuum
  8. filtrationfilter funnel

Sources & evidence

ORD record
ord-6f5f675b44464d16bcc875edda6beac8
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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