Dimethylformamide → HCID 86715092, compound

HRID 533899Notes

Reaction equation

HRID 533899 reaction equation
[CH:1]1([CH2:4][CH2:5][OH:6])[CH2:3][CH2:2]1.CN(C=O)C.[H-].[Na+].[Br:14][C:15]1[CH:16]=[CH:17][C:18](F)=[N:19][CH:20]=1>CC(=O)OCC.O>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:6][CH2:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[N:19][CH:20]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1376422-Cyclopropylethan-1-olHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 86715092HCID 86715092, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-cyclopropyl-ethanol (4.1 g) and DMF (15 mL) under argon was treated with NaH (60% in oil, 0.45 g). After 4 hours 5-bromo-2-fluoro-pyridine (3.0 g) was added at 0° C. After 4 hours at room temperature, the mixture was distributed between water and EA. The organic phase was washed twice (water), dried (Na2SO4) and concentrated. The residue was purified by chromatography (SiO2; EA/heptane 1:4) to provide the subtitle compound. MS ESI+: m/z=242 [M+H]+.

Workup

  1. washThe organic phase was washed twice (water)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography (SiO2; EA/heptane 1:4)

Sources & evidence

ORD record
ord-27e5b071444d401ba37c6432d2d3b024
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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