Sodium Carbonate → HCID 67034134, compound

HRID 539100Notes

Reaction equation

HRID 539100 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[C@@H:15]([C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]=4)[CH2:14][O:13][C:12]3=[O:23])=[N:7][C:6]=12.[F:24][C:25]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[CH:27][C:26]=1[C:40]1[N:44]=[CH:43][N:42]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[N:41]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[F:24][C:25]1[CH:30]=[C:29]([C:2]2[CH:3]=[N:4][N:5]3[CH:10]=[CH:9][C:8]([N:11]4[C@@H:15]([C:16]5[CH:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]=5)[CH2:14][O:13][C:12]4=[O:23])=[N:7][C:6]=23)[CH:28]=[CH:27][C:26]=1[C:40]1[N:44]=[CH:43][N:42]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[N:41]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 67034012HCID 67034012, compoundHCID 67034163(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one

Product 1

HCID 67034134HCID 67034134, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one (6.7 g, 18 mmol) and 3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole (11 g, 27 mmol) in dioxane (150 mL) was added sodium carbonate (44 ml, 89 mmol) (2 M in water) and the reaction mixture bubbled with nitrogen gas for 30 minutes, followed by addition of 750 mg each of Pd2 dba3 and X-phos, and the reaction heated to 80° C. while the nitrogen purge continued. The reaction was poured into water (150 mL) and extracted with ethyl acetate (400 mL). The organic layer was washed with water (100 mL), brine (100 mL), dried over MgSO4 and concentrated in vacuo. The material was chromatographed using a gradient of 70% EtOAc/DCM to EtOAc as eluent to yield (S)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one (5.8 g, 9.8 mmol, 55% yield).

Workup

  1. customthe reaction mixture bubbled with nitrogen gas for 30 minutes
  2. additionfollowed by addition of 750 mg each of Pd2 dba3 and X-phos
  3. custompurge
  4. additionThe reaction was poured into water (150 mL)
  5. extractionextracted with ethyl acetate (400 mL)
  6. washThe organic layer was washed with water (100 mL), brine (100 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe material was chromatographed

Sources & evidence

ORD record
ord-4a89b9010f684c54ba0be1b9bc854a34
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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