Dimethyl Sulfoxide → HCID 59255486, compound

HRID 1691043Notes

Reaction equation

HRID 1691043 reaction equation
CS(C)=O.[F:5][C:6]1[CH:7]=[CH:8][C:9]([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)=[N:10][CH:11]=1.[BH4-].[Na+]>C(O)(=O)C>[F:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][N+:22]([O-:24])=[O:23])=[CH:16][CH:15]=2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 59255506HCID 59255506, compound

Product 1

HCID 59255486HCID 59255486, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a dimethyl sulfoxide (49 mL) solution of 5-fluoro-2-(4-((E)-nitro-vinyl)benzyloxy)-pyridine (2.9 g, 10.6 mmol) described in Manufacturing Example 56-1-3 and acetic acid (2.9 mL) was added sodium borohydride (642 mg, 17 mmol) at room temperature while cooling appropriately. This mixture was stirred for 1 hour at room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with 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 NH-silica gel column chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (1.63 g, 56%).

Workup

  1. temperaturewhile cooling appropriately
  2. customThis mixture was partitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with 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 NH-silica gel column chromatography (heptane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-7b343b39364144e59366bc3b3911e80d
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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