Acetic Acid → 2-(3-Fluoro-4-(2-nitro-ethyl)-phenoxymethyl)-pyridine

HRID 78076Notes

Reaction equation

HRID 78076 reaction equation
CS(C)=O.[F:5][C:6]1[CH:7]=[C:8]([CH:17]=[CH:18][C:19]=1/[CH:20]=[CH:21]/[N+:22]([O-:24])=[O:23])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.C(O)(=O)C.[BH4-].[Na+]>O>[F:5][C:6]1[CH:7]=[C:8]([CH:17]=[CH:18][C:19]=1[CH2:20][CH2:21][N+:22]([O-:24])=[O:23])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 592552272-(3-Fluoro-4-((E)-2-nitro-vinyl)-phenoxymethyl)pyridine

Product 1

HCID 592554052-(3-Fluoro-4-(2-nitro-ethyl)-phenoxymethyl)-pyridineYield 50.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethyl sulfoxide (20.0 mL) solution of 2-(3-fluoro-4-((E)-2-nitro-vinyl)-phenoxymethyl)pyridine (1.20 g) described in Manufacturing Example 95-1-2 and acetic acid (1.00 mL) was added sodium borohydride (249 mg, 6.57 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 30 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, followed by crystallization with an ethyl acetate-heptane system and filtration to obtain the title compound (614 mg, 50.7%).

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. customfollowed by crystallization with an ethyl acetate-heptane system and filtration

Sources & evidence

ORD record
ord-330b22863fd04c0fb95a52c7eacb26dc
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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