HCID 86616914, compound → HCID 86616913, compound

HRID 1864638Notes

Reaction equation

HRID 1864638 reaction equation
[H][H].[NH2:3][C:4]1[C:9]([N+:10]([O-])=O)=[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:16]([F:27])[CH:15]=2)[CH:7]=[CH:6][N:5]=1>C(O)C.CCOC(C)=O.[Pd]>[NH2:3][C:4]1[C:9]([NH2:10])=[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:26])[C:22]([F:23])([F:24])[F:25])=[C:16]([F:27])[CH:15]=2)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 2

HCID 86616914HCID 86616914, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86616913HCID 86616913, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Method D2 (using hydrogen). N-(4-(2-amino-3-nitropyridin-4-yl-oxy)-2-fluorophenyl)-2,2,2-trifluoroacetamide (540 mg, 1.5 mmol) was dissolved in ethanol (15 mL) and AcOEt (5 mL). Palladium 10% on activated carbon (150 mg) was added and the reaction mixture was stirred for 2 hours under hydrogen atmosphere. The catalyst was filtered off and the filtrate evaporated to afford the title compound (490 mg, 100%). 1H-NMR (δ, ppm, DMSO-d6): 4.65 (s, 2H, NH2,Py3), 5.86 (s, 2H, NH2,Py2), 6.23 (d, 1H, HPy,6, J=5.71 Hz), 6.85 (d, 1H, Harom,Ph, J=8.80 Hz), 7.01 (d, 1H, Harom,Ph, J=11.51 Hz), 7.32 (d, 1H, HPy,5, J=5.71 Hz), 7.45 (t, 1H, Harom,Ph, J=8.76 hz), 11.37 (s, 1H, NHCOCF3).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-a40d2780e8b74f27a9d96f394af39b95
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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