Sodium hydride → 5-Bromo-2-(cyclopropylmethoxy)pyridine

HRID 533901Notes

Reaction equation

HRID 533901 reaction equation
[CH2:1]1[CH2:3][CH:2]1[CH2:4][OH:5].[H-].[Na+].[Br:8][C:9]1[CH:10]=[CH:11][C:12](F)=[N:13][CH:14]=1>CN(C=O)C.CC(=O)OCC>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:5][CH2:4][CH:2]2[CH2:3][CH2:1]2)=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 219142795-Bromo-2-(cyclopropylmethoxy)pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-cyclopropyl-methanol (6.15 g) and DMF (12 mL) was added NaH (60% in mineral oil, 1.5 g) at 0° C. After stirring for 4 hours at r.t. the mixture was diluted with DMF (5 mL) and 5-bromo-2-fluoro-pyridine (6.00 g) was slowly added keeping the reaction temperature below 30° C. After 30 minutes at r.t. the mixture was heated to 130° C. for 1 hour by microwave irradiation. After cooling to r.t. the mixture was diluted with EA and washed with water (3 times). The organic phase was dried (Na2SO4) and concentrated. The residue was purified by SGC to provide the subtitle compound. MS ESI+: m/z=228 [M+H]+.

Workup

  1. additionwas slowly added
  2. customthe reaction temperature below 30° C
  3. temperatureAfter 30 minutes at r.t. the mixture was heated to 130° C. for 1 hour by microwave irradiation
  4. temperatureAfter cooling to r.t. the mixture
  5. washwashed with water (3 times)
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by SGC

Sources & evidence

ORD record
ord-700b9e94a18e43d29af1373dce8e036c
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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