HCID 68694189, compound → HCID 24760660, compound

HRID 1989668Notes

Reaction equation

HRID 1989668 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[CH:25]=3)[CH:19]=2)[CH:3]=1.[H][H]>C1COCC1.CO.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]3[CH:25]=[C:26]([NH2:30])[CH:27]=[CH:28][CH:29]=3)[CH:19]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 68694189HCID 68694189, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 24760660HCID 24760660, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of the above prepared 4-methyl-2′-(3-nitro-phenyl)-6-(4-trifluoromethylphenyl)-[2,4′]bipyridinyl (1.12 g, 3.0 mmol) in THF-MeOH 1:1 (100 mL) and 10% palladium on carbon (1 mol %) was hydrogenated (1 bar hydrogen) at 23° C. for 2 h. The catalyst was filtered off, washed with MeOH and the filtrate was completely evaporated totally to leave a crude product, which was purified by trituration with diethyl ether to give the title compound as a light brown solid (0.914 g, 88%). MS (ISP) 406.5 [(M+H)+]; mp 87° C. (dec.).

Workup

  1. additionA mixture of the
  2. customat 23° C.
  3. customfor 2 h
  4. filtrationThe catalyst was filtered off
  5. washwashed with MeOH
  6. customthe filtrate was completely evaporated totally
  7. customto leave a crude product, which
  8. customwas purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-9645aa0062fd49a99e244af8102cad2c
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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