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

HRID 539112Notes

Reaction equation

HRID 539112 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]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:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[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 67033115(S)-4-(2-chlorophenyl)oxazolidin-2-one

Product 1

HCID 67035102(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-chlorophenyl)oxazolidin-2-oneYield 34.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (S)-4-(2-chlorophenyl)oxazolidin-2-one (265 mg, 1.34 mmol) in DMF (10 mL) was added sodium hydride (59.0 mg, 1.48 mmol) and the reaction was stirred at ambient temperature for 1 hour. 3-Bromo-5-chloropyrazolo[1,5-a]pyrimidine (343 mg, 1.48 mmol) was added in one portion and the reaction was stirred at ambient temperature for 18 hours. Ice was added followed by ammonium chloride (aqueous) and the resulting suspension was filtered and washed with water. After drying, (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-chlorophenyl)oxazolidin-2-one (180 mg, 34.1% yield) was isolated as a pale yellow solid.

Workup

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

Sources & evidence

ORD record
ord-18be7df5b3c94d3186327862983dac48
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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