Sodium hydride → HCID 86715119, compound

HRID 533933Notes

Reaction equation

HRID 533933 reaction equation
[H-].[Na+].[CH:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[Br:8][C:9]1[C:10](F)=[N:11][CH:12]=[C:13]([I:15])[CH:14]=1>C1COCC1>[Br:8][C:9]1[C:10]([O:7][CH2:6][CH:3]2[CH2:5][CH2:4]2)=[N:11][CH:12]=[C:13]([I:15])[CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 462383963-Bromo-2-fluoro-5-iodopyridine

Product 1

HCID 86715119HCID 86715119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (60% in mineral oil, 4.32 g) in THF (300 mL) was added cyclopropylmethanol (5.83 g) at 0° C. and the mixture was stirred for 30 min at 0° C. A solution of 3-bromo-2-fluoro-5-iodopyridine (16.3 g) in THF (50 mL) was added to the suspension at 0° C. The suspension was allowed to warm to r.t. and stirred for 18 h. The suspension was poured into ice water and then extracted with EA (200 mL×3). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and evaporation of the solvent, the residue was purified by SGC (eluent: PE) to give the subtitle compound. MS ESI+: m/z=354 [M+H]+.

Workup

  1. temperatureto warm to r.t.
  2. stirringstirred for 18 h
  3. extractionextracted with EA (200 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and evaporation of the solvent
  7. customthe residue was purified by SGC (eluent: PE)

Sources & evidence

ORD record
ord-390e6eaa68334c01932abca8ab0e94a9
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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