Benzene, 1-bromo-2-(trifluoromethyl)- → HCID 89586245, compound

HRID 1747817Notes

Reaction equation

HRID 1747817 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[C:17](=[O:18])[CH:16]=[CH:15][N:14]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[N:13]=3)=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]([F:35])([F:34])[F:33].CC(C)([O-])C.[Na+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])O.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[C:1]1([N:7]2[C:11]([C:12]3[C:17](=[O:18])[CH:16]=[CH:15][N:14]([CH:19]4[CH2:24][CH2:23][N:22]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:32]([F:35])([F:34])[F:33])[CH2:21][CH2:20]4)[N:13]=3)=[CH:10][CH:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 9806Benzene, 1-bromo-2-(trifluoromethyl)-HCID 516892Sodium BicarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 68014851HCID 68014851, compound

Product 1

HCID 89586245HCID 89586245, compoundYield 11.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-(1-phenyl-1H-pyrazol-5-yl)-1-piperidin-4-ylpyridazin-4(1H)-one (25.7 mg), 2-bromobenzotrifluoride (27 mg), Pd2(dba)3 (1.8 mg), sodium tert-butoxide (8.8 mg), X-phos (1.9 mg) and toluene (1.0 mL) was heated using a microwave reactor (Synthos3000) at 120° C. for 10 min. To the reaction mixture was added 5% sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate (the extract was separated by an organic layer-separation filter). The extract was distilled by blowing air at 60° C., and the residue was dissolved in DMSO. The solution was purified by preparative HPLC (column: Hydrosphere, solvent: 10 mM NH4HCO3/MeCN). The obtained eluate containing the title compound was concentrated by blowing air at 60° C. to give the title compound (4.2 mg).

Workup

  1. temperaturewas heated
  2. customat 120° C.
  3. customfor 10 min
  4. extractionthe mixture was extracted with ethyl acetate (the extract
  5. customwas separated by an organic layer-separation
  6. filtrationfilter)
  7. distillationThe extract was distilled
  8. customat 60° C.
  9. dissolutionthe residue was dissolved in DMSO
  10. customThe solution was purified by preparative HPLC (column
  11. additionThe obtained eluate containing the title compound
  12. concentrationwas concentrated
  13. customat 60° C.

Sources & evidence

ORD record
ord-254235594b844c78bf644fbcb34e60a0
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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