Sodium hydride → (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(3-chlorophenyl)oxazolidin-2-one

HRID 539116Notes

Reaction equation

HRID 539116 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[NH:9]2)[CH:5]=[CH:6][CH:7]=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.[Cl-].[NH4+]>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:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[CH2:12][O:11][C:10]3=[O:13])=[N:22][C:21]=12

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidineHCID 67033385(S)-4-(3-chlorophenyl)oxazolidin-2-one

Product 1

HCID 67034388(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(3-chlorophenyl)oxazolidin-2-oneYield 45.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (S)-4-(3-chlorophenyl)oxazolidin-2-one (278 mg, 1.41 mmol) in DMF (10 mL) was added sodium hydride (56.8 mg, 1.42 mmol) and the reaction was stirred at ambient temperature for 1 hour. 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (300 mg, 1.29 mmol) was added at once and the reaction was stirred at ambient temperature for 18 hours. Ice was added followed by ammonium chloride (aqueous), and the resulting suspension filtered and washed with water. After drying, (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(3-chlorophenyl)oxazolidin-2-one (231 mg, 45.5% yield) was isolated as a pale yellow solid.

Workup

  1. stirringwas stirred at ambient temperature for 18 hours
  2. additionIce was added
  3. filtrationthe resulting suspension filtered
  4. washwashed with water
  5. customAfter drying

Sources & evidence

ORD record
ord-c1ec90ce3acb4d9b99797f0dc8a25f3b
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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