Water → HCID 25216631, compound

HRID 878852Notes

Reaction equation

HRID 878852 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9](=[O:34])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][C:19]([C:25]4[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=4)([C:21]([F:24])([F:23])[F:22])[O:18][N:17]=3)=[CH:12][C:11]=2[CH3:33])=[N:6][CH:7]=1.O.N.O.[CH3:38][N:39](C)C(=O)C>[C-]#N.[Zn+2].[C-]#N.[Zn].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(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:38]([C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9](=[O:34])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][C:19]([C:25]4[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=4)([C:21]([F:23])([F:22])[F:24])[O:18][N:17]=3)=[CH:12][C:11]=2[CH3:33])=[N:6][CH:7]=1)#[N:39]

Participants

9

Reactant 4

HCID 962WaterHCID 31374DimethylacetamideHCID 12896473Azane;hydrateHCID 86654457HCID 86654457, compound

Product 1

HCID 25216631HCID 25216631, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

In a solution of 0.20 g of N-(5-bromo-2-pyrimidinyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoic acid amide synthesized in Step 1 of Synthetic Example 13 in 3 mL of N,N-dimethylacetamide, 0.082 g of zinc cyanide, 0.011 g of zinc, 0.013 g of tris(dibenzylideneacetone)dipalladium and 0.015 g of 1,1′-bis(diphenylphosphino)ferrocene were added, and stirred under nitrogen atmosphere at 100° C. for 2 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and 20 mL of concentrated ammonia water and 20 mL of water were added, and extracted with ethyl acetate (20 mL×2). The organic phases were washed with water, and dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:1) to obtain 0.15 g of the aimed product as white crystal.

Workup

  1. customAfter the completion of the reaction
  2. waitthe reaction mixture was left
  3. temperaturecooled to room temperature
  4. extractionextracted with ethyl acetate (20 mL×2)
  5. washThe organic phases were washed with water
  6. dry with materialdried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-cfff58890c0847659f7bf0f28229a074
Source dataset
uspto-grants-2015_03
Patent number
US08987464B2

Reaction notes

Loading…