Cesium carbonate → 1342905-27-4

HRID 1755276Notes

Reaction equation

HRID 1755276 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[CH:9][NH:8][N:7]=1)=[O:5])C.[O:11]1[CH2:16][CH2:15][CH:14](OS(C)(=O)=O)[CH2:13][CH2:12]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[O:11]1[CH2:16][CH2:15][CH:14]([N:8]2[CH:9]=[CH:10][C:6]([C:4]([OH:3])=[O:5])=[N:7]2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11344352Oxan-4-yl methanesulfonateHCID 178469268HCID 178469268, compound

Product 1

HCID 644495421342905-27-4Yield 21.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A vial was charged with ethyl-1H-pyrazole-3-carboxylate (3.74 g, 26.7 mmol), the crude methanesulfonic acid tetrahydro-pyran-4-yl ester (29.4 mmol), Cs2CO3 (17.4 g, 53.4 mmol), and DMF (100 mL). The reaction mixture was heated to 80° C. and stirred overnight. The reaction was then partitioned between CH2Cl2 (250 mL) and water (250 mL), and the organic layer was washed with water (5×250 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product containing 2 regioisomers was purified via flash chromatography on silica gel (95:5-50:50 hexanes:EtOAc) and the later eluting isomer was isolated. This was purified on silica gel a second time (85:15-60:40 hexanes:EtOAc) to give the pure desired product (1.14 g, 19%).

Workup

  1. customThe reaction was then partitioned between CH2Cl2 (250 mL) and water (250 mL)
  2. washthe organic layer was washed with water (5×250 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionThe crude product containing 2 regioisomers
  7. customwas purified via flash chromatography on silica gel (95:5-50:50 hexanes:EtOAc)
  8. customthe later eluting isomer was isolated
  9. customThis was purified on silica gel a second time (85:15-60:40 hexanes:EtOAc)

Sources & evidence

ORD record
ord-7aeaadcd81fe49a8a6b50290dafc4242
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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