HCID 70976239, compound → HCID 70975647, compound

HRID 1484513Notes

Reaction equation

HRID 1484513 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=2)=[CH:4][C:3]=1[O:18][C:19]([F:22])([F:21])[F:20]>C1COCC1.[Pd]>[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[N:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=2)=[CH:4][C:3]=1[O:18][C:19]([F:21])([F:20])[F:22]

Participants

4

Reactant 1

HCID 70976239HCID 70976239, compound2×

Product 1

HCID 70975647HCID 70975647, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2-[4-methyl-3-(trifluoromethoxy)phenoxy]-5-nitropyridine (Intermediate 30, 594 mg, 1.89 mmol) and Pd/C 5% w/w (40 mg) in THF (3 mL) was hydrogenated under 5 bar of H2, at 35° C. for 18 hrs. The mixture was filtered to remove the catalyst, diluted with ethyl acetate (10 mL) and washed with an aqueous 13% solution of NaCl (10 mL). The organic layer, dried over Na2SO4, was evaporated to give the title compound (475 mg) as brown oil.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. additiondiluted with ethyl acetate (10 mL)
  4. washwashed with an aqueous 13% solution of NaCl (10 mL)
  5. dry with materialThe organic layer, dried over Na2SO4
  6. customwas evaporated

Sources & evidence

ORD record
ord-8089388989324c399a28af4a13c61e06
Source dataset
uspto-grants-2016_08
Patent number
US09422252B2

Reaction notes

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