Phenylacetylene → HCID 57524504, compound

HRID 623835Notes

Reaction equation

HRID 623835 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:15]2[N:19]=[CH:18][NH:17][N:16]=2)[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)([CH3:3])[CH3:2].[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)#[CH:21].[OH-].[K+].CCOC(C)=O.CCCCCC>CS(C)=O>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:15]2[N:19]=[CH:18][N:17](/[CH:21]=[CH:20]\[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:16]=2)[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 10821PhenylacetyleneHCID 14797Potassium HydroxideHCID 21226206Ethyl acetate hexaneHCID 178458204HCID 178458204, compound

Product 1

HCID 57524504HCID 57524504, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a 10 mL microwave seal tube 3-(3-isopropoxy-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazole (0.5 g, 1.0 eq.) and ethynylbenzene (0.25 mL, 1.2 eq.) were dissolved in DMSO (5 mL). KOH (0.29 g, 2.5 eq.) was added and the reaction mixture was irradiated at 120° C. for 45 min in CEM Microwave. The completion of the reaction was confirmed by TLC using 30% EtOAc-hexane as mobile phase. Reaction mixture was quenched into ice water slurry. Compound was extracted by ethyl acetate. Organic layer was washed with brine, dried over Na2SO4, filtered and concentrated by rotary evaporation (40° C., 20 mmHg) to afford 0.373 g of brown oil. The crude reaction mixture was purified by column chromatography using silica 60/120 using ethyl acetate:hexane as mobile phase. The column was packed in hexane and started eluting in ethyl acetate in gradient manner starting with fraction collection from 5% to 10% ethyl acetate in hexane. Compound started eluting with 14% ethyl acetate in hexane. Fraction containing such TLC profile was collected together to obtain pure compound (30 mg); LCMS (%): Retention time for cis 4.7970 min (100.0%); For trans 3.975 min (98.06%).

Workup

  1. customthe reaction mixture was irradiated at 120° C. for 45 min in CEM Microwave
  2. customReaction mixture
  3. customwas quenched into ice water slurry
  4. extractionCompound was extracted by ethyl acetate
  5. washOrganic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation (40° C., 20 mmHg)

Sources & evidence

ORD record
ord-2dd56512053a41da80fa507cbddaf544
Source dataset
uspto-grants-2016_04
Patent number
US09303000B2

Reaction notes

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