HCID 58938125, compound → HCID 58938115, compound

HRID 2246445Notes

Reaction equation

HRID 2246445 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:5]=[C:4]([C:18]#[N:19])[C:3]=1[N+:20]([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:20][C:3]1[C:4]([C:18]#[N:19])=[N:5][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 58938125HCID 58938125, compound

Product 1

HCID 58938115HCID 58938115, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring suspension of 4-amino-3-nitro-6-(3-trifluoromethyl-phenyl)-pyridine-2-carbonitrile (300 mg, 0.97 mmol) in ethyl acetate (80 ml) was added 10% palladium on carbon (wet) (300 mg, 2.82 mmol). The vessel was purged with hydrogen (balloon) and stirred at room temperature for 1.5 hrs. Reaction mixture was filtered through celite and concentrated in vacuo to give the title compound as a dark orange solid (240 mg, 89%). 1H NMR (MeOD): δ 8.15 (s, 1H), 8.04 (d, 1H), 7.58-7.65 (m, 2H), 7.18 (s, 1H). MS m/z 279.3 (M+1).

Workup

  1. customThe vessel was purged with hydrogen (balloon)
  2. customReaction mixture
  3. filtrationwas filtered through celite and
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bea0773e757f44b3b6f3e4f07f162d1f
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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