N-bromobutanimide → HCID 85885309, compound

HRID 968664Notes

Reaction equation

HRID 968664 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:10]=[C:6]2[N:5]=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>ClCCl>[Br:17][C:10]1[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][N:7]2[C:2]([Cl:1])=[CH:3][CH:4]=[N:5][C:6]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1272611977493-88-0

Product 1

HCID 85885309HCID 85885309, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-Chloro-2-phenylpyrazolo[1,5-α]pyrimidine (0.1 g, 0.44 mmol, prepared as described in J. Med. Chem. 1981, 24, 610) was dissolved in dichloromethane (5 mL) and to this solution was added N-bromosuccinimide (108 mg, 0.61 mmol). The resulting reaction mixture was stirred for 30 minutes. Additional dichloromethane was added and the mixture was extracted with sodium hydroxide (1N), water and a saturated aqueous sodium chloride solution. The organic phase was dried over magnesium sulfate, filtered and concentrated. The resulting solid was purified by silica gel chromatography (ethyl acetate:hexane 1:2) to give 110 mg (82%) of 3-bromo-7-chloro-2-phenylpyrazolo[1,5-α]pyrimidine as a yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. extractionthe mixture was extracted with sodium hydroxide (1N), water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting solid was purified by silica gel chromatography (ethyl acetate:hexane 1:2)

Sources & evidence

ORD record
ord-dba069bb252d4b90971e273e29976acd
Source dataset
uspto-grants-2007_12
Patent number
US07304068B2

Reaction notes

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