Sodium Carbonate → HCID 86667831, compound

HRID 539132Notes

Reaction equation

HRID 539132 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:26]=[C:27](B(O)O)[CH:28]=[CH:29][C:30]=1[CH:31]=[O:32].C(=O)([O-])[O-].[Na+].[Na+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:24][C:25]1[CH:26]=[C:27]([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:29][C:30]=1[CH:31]=[O:32]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27786543-Fluoro-4-formylphenylboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67034163(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one

Product 1

HCID 86667831HCID 86667831, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 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 (0.500 g, 1.32 mmol) in dioxane (8 mL) purged continuously with nitrogen gas was added 3-fluoro-4-formylphenylboronic acid (0.333 g, 1.98 mmol) and 2.0 M sodium carbonate aqueous solution (1.98 mL, 3.97 mmol). To the reaction was added Pd2 dba3 (0.242 g, 0.264 mmol) and X-Phos (0.126 g, 0.264 mmol) and the reaction stirred at 80° C. for 1 hour. After cooling, the reaction was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water and brine, dried, and concentrated under vacuum. The residue was purified by preparative TLC (50% EtOAc/hexane) to give (S)-2-fluoro-4-(5-(4-(5-fluoropyridin-2-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzaldehyde (0.47 g, 84% yield) as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. customthe reaction was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by preparative TLC (50% EtOAc/hexane)

Sources & evidence

ORD record
ord-1d9c19a747e44c1ea29f2b6930d5a0ed
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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