HCID 68689159, compound → HCID 24760585, compound

HRID 1928334Notes

Reaction equation

HRID 1928334 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=3)[CH: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.CO.[Pd]>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=3)[CH: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 68689159HCID 68689159, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 24760585HCID 24760585, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 6-methyl-2′-(3-nitro-phenyl)-4-(4-trifluoromethyl-phenyl)-[2,4′]bipyridinyl (example 306) (6.6 g, 15.15 mmol) in THF-MeOH 1:1 (300 mL) and 10% palladium on carbon (10 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 triturated with diethyl ether and dried in HV to give the title compound as a light brown solid (6.0 g, 97%). MS (ISP) 406.3 [(M+H)+]; mp 162° C. (dec.).

Workup

  1. customat 23° C.
  2. customfor 2 h
  3. filtrationThe catalyst was filtered off
  4. washwashed with MeOH
  5. customthe filtrate was completely evaporated totally
  6. customto leave a crude product, which
  7. customwas triturated with diethyl ether
  8. customdried in HV

Sources & evidence

ORD record
ord-2422f93d6a4748119188b9485cac0bed
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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