Water → (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(4-fluorophenyl)oxazolidin-2-one

HRID 538972Notes

Reaction equation

HRID 538972 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[NH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[Br:16][C:17]1[CH:18]=[N:19][N:20]2[CH:25]=[CH:24][C:23](Cl)=[N:22][C:21]=12.O>CN(C=O)C>[Br:16][C:17]1[CH:18]=[N:19][N:20]2[CH:25]=[CH:24][C:23]([N:9]3[C@@H:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH2:12][O:11][C:10]3=[O:13])=[N:22][C:21]=12

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidineHCID 67034376HCID 67034376, compound

Product 1

HCID 67034438(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(4-fluorophenyl)oxazolidin-2-oneYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-4-(4-fluorophenyl)oxazolidin-2-one (0.43 g, 2.4 mmol) in DMF (10 mL) was added sodium hydride (0.095 g, 2.4 mmol) and the reaction stirred at ambient temperature for 30 minutes. 3-Bromo-5-chloropyrazolo[1,5-a]pyrimidine (0.50 g, 2.2 mmol) was added and the reaction was stirred for 2 hours at ambient temperature. The reaction mixture was poured into water (100 mL) and extracted into ether (2×100 mL). The organic layer was washed with brine (2×20 mL), dried over MgSO4 and concentrated under vacuum. The crude material was purified by silica gel chromatography, eluting with 2% EtOAc/DCM to yield (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(4-fluorophenyl)oxazolidin-2-one (0.35 g, 43%).

Workup

  1. stirringthe reaction was stirred for 2 hours at ambient temperature
  2. extractionextracted into ether (2×100 mL)
  3. washThe organic layer was washed with brine (2×20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with 2% EtOAc/DCM

Sources & evidence

ORD record
ord-70814e6bef3d416d98b51f704881d17d
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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