Water → HCID 86699776, compound

HRID 1777383Notes

Reaction equation

HRID 1777383 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[N:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][CH:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24].O>CN(C=O)C>[CH2:23]([O:22][CH:21]([O:25][CH2:26][CH3:27])[CH2:20][N:10]1[CH:11]=[CH:12][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=2)=[N:9]1)[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 178505521HCID 178505521, compound

Product 1

HCID 86699776HCID 86699776, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-fluoro-2-(1H-pyrazol-3-yl)pyridine obtained in Reference Example 10 (11.7 g, 58.6 mmol) in DMF (195 mL), Cs2CO3 (57.3 g, 0.18 mol) and 2-bromo-1,1-diethoxyethane (11.5 mL, 76.2 mmol) were stirred for 18 hours at 80° C. The reaction mixture was allowed to cool to room temperature, then water was added thereto, followed by extraction with EtOAc. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over MgSO4, then the drying agent was filtered off, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (HP-Sil 50 g, hexane/EtOAc=88/12 to 35/65) to obtain the title compound (8.2 g) (colorless oil).

Workup

  1. temperatureto cool to room temperature
  2. extractionfollowed by extraction with EtOAc
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over MgSO4
  5. filtrationthe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by column chromatography (HP-Sil 50 g, hexane/EtOAc=88/12 to 35/65)

Sources & evidence

ORD record
ord-0f35504d6f5b41e480b58c4afada867d
Source dataset
uspto-grants-2016_02
Patent number
US09266870B2

Reaction notes

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