HCID 68691292, compound → 3-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-phenylamine

HRID 1928356Notes

Reaction equation

HRID 1928356 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=3)[N:9]=2)[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH:3]=1.[H][H]>C1COCC1.CCO.[Pd]>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=3)[N:9]=2)[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:30])[F:32])=[CH:25][CH:24]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 68691292HCID 68691292, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 247605873-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-phenylamineYield 80.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A mixture of the above prepared 6-methyl-6′-(3-nitro-phenyl)-4-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl (3.4 g, 7.81 mmol) in THF-EtOH 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 EtOH and the filtrate was completely evaporated totally to leave a crude product, which was purified by silica gel column chromatography with heptane/EtOAc, followed by trituration with diethyl ether to give the title compound as a white solid (2.55 g, 80%). MS (ISP) 406.3 [(M+H)+]; mp 167° C.

Workup

  1. additionA mixture of the
  2. customat 23° C.
  3. customfor 2 h
  4. filtrationThe catalyst was filtered off
  5. washwashed with EtOH
  6. customthe filtrate was completely evaporated totally
  7. customto leave a crude product, which
  8. customwas purified by silica gel column chromatography with heptane/EtOAc

Sources & evidence

ORD record
ord-d043e61a5a5d4d37b6532326cce302d2
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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