Water → 3-Bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine

HRID 570140Notes

Reaction equation

HRID 570140 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:11]3[N:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.O>C(Cl)(Cl)Cl>[Br:17][C:16]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][N:10]2[CH:15]=[CH:14][CH:13]=[N:12][C:11]=12

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 692972612-(4-Fluorophenyl)pyrazolo[1,5-a]pyrimidine

Product 1

HCID 837474383-Bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidineYield 76.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine (5.8 g, 0.027 mol) in chloroform (60 mL) is added, at 0° C., N-bromosuccinimide (4.8 g, 0.027 mol). The mixture is stirred at room temperature for 1 h 30. The reaction mixture is then poured into water and extracted with dichloromethane (3×100 mL). The organic layer is dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material is filtered through a short pad of silica. 6 g (75%) of 3-bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine are obtained as a brown solid which is used in the next step without further purification.

Workup

  1. extractionextracted with dichloromethane (3×100 mL)
  2. dry with materialThe organic layer is dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe crude material is filtered through a short pad of silica

Sources & evidence

ORD record
ord-283af891170a41819dfe6340dae04fa3
Source dataset
uspto-grants-2015_05
Patent number
US09023844B2

Reaction notes

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