Dimethyl Sulfoxide → 5-Fluoro-2-(3-fluoro-4-(2-nitro-ethyl)-phenoxymethyl)pyridine

HRID 78080Notes

Reaction equation

HRID 78080 reaction equation
CS(C)=O.O1CCCC1.[F:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[N+:27]([O-:29])=[O:28])=[C:21]([F:30])[CH:20]=2)=[N:15][CH:16]=1.[BH4-].[Na+]>O.C(O)(=O)C>[F:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][N+:27]([O-:29])=[O:28])=[C:21]([F:30])[CH:20]=2)=[N:15][CH:16]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 592550775-Fluoro-2-(3-fluoro-4-((E)-2-nitro-vinyl)phenoxymethyl)-pyridine

Product 1

HCID 592552775-Fluoro-2-(3-fluoro-4-(2-nitro-ethyl)-phenoxymethyl)pyridineYield 34.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a dimethyl sulfoxide (20.0 mL)-tetrahydrofuran (5.00 mL) solution of 5-fluoro-2-(3-fluoro-4-((E)-2-nitro-vinyl)-phenoxymethyl)-pyridine (1.00 g, 3.42 mmol) described in Manufacturing Example 96-1-2 and acetic acid (1.00 mL) was added sodium borohydride (207 mg, 5.47 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 10 minutes at room temperature. Water was then added dropwise at room temperature while cooling appropriately. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was crystallized with an ethyl acetate: heptane system and filtered to obtain the title compound (346 mg, 34.4%).

Workup

  1. temperaturewhile cooling appropriately under nitrogen atmosphere
  2. temperaturewhile cooling appropriately
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was crystallized with an ethyl acetate
  9. filtrationheptane system and filtered

Sources & evidence

ORD record
ord-0b1cca48eaf94ed0899c7f9db18bd1f6
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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