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

HRID 1891662Notes

Reaction equation

HRID 1891662 reaction equation
C(O)(=O)C.[F:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[N+:22]([O-:24])=[O:23])=[CH:16][CH:15]=2)[CH:7]=1.[BH4-].[Na+]>CS(C)=O>[F:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][N+:22]([O-:24])=[O:23])=[CH:18][CH:19]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 59255074HCID 59255074, compound

Product 1

HCID 592550924-Fluoro-2-(4-(2-nitro-ethyl)-benzyloxy)-pyridineYield 55.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To an acetic acid (1.7 mL) and dimethyl sulfoxide (29 mL) solution of 4-fluoro-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine (1.72 g, 6.27 mmol) described in Manufacturing Example 59-1-3 was added sodium borohydride (380 mg, 10 mmol) at room temperature while cooling appropriately. This mixture was stirred for 5 hours at room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, 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 purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1) to obtain the title compound (960 mg, 55%).

Workup

  1. temperaturewhile cooling appropriately
  2. customThis mixture was partitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed 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 purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1)

Sources & evidence

ORD record
ord-ab7aa943c55944e1803f1f6d417f118a
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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