Toluene → HCID 15452561, compound

HRID 396418Notes

Reaction equation

HRID 396418 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]([NH2:15])=[CH:13][C:12]([C:16]#[N:17])=[N:11]1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.O.C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:23]2[CH:24]=[CH:25][C:20]([C:19]([F:30])([F:29])[F:18])=[CH:21][CH:22]=2)[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]([NH2:15])=[CH:13][C:12]([C:16]#[N:17])=[N:11]1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 18171853HCID 18171853, compound

Product 1

HCID 15452561HCID 15452561, compound

Reagents, catalysts & solvents 3

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1-(2,6-dichloro-4-bromophenyl)-3-cyano-5-aminopyrazole (45 g, prepared according to procedures reported in U.S. Pat. No. 5,232,940), 4-trifluoromethylphenylboronic acid (45 g), 2 M of Na2CO3 (75 mL), tris-(dibenzylideneacetone) dipalladium (6.4 g), toluene and ethanol was heated at 130° C. for 25 hours. After cooling to 20° C., the mixture was poured into water and extracted with diethyl ether. The ether solutions were combined, dried, filtered and the filtrate concentrated and purified via chromatography. The desired product as a solid (30.6 g, mp 195-199° C.) was obtained.

Workup

  1. customprepared
  2. extractionextracted with diethyl ether
  3. customdried
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. custompurified via chromatography

Sources & evidence

ORD record
ord-a785019164e24a7db509b6bdc7436643
Source dataset
uspto-grants-2003_08
Patent number
US06608093B2

Reaction notes

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