Potassium Carbonate → 5-Methylsulfonyl-2-[5-(4-acetylenyl-phenyl)-3-trifluoromethyl-1h-pyrazol-1-yl]pyridine

HRID 1634277Notes

Reaction equation

HRID 1634277 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=3)=[CH:14][C:13]([C:23]([F:26])([F:25])[F:24])=[N:12]2)=[N:9][CH:10]=1)(=[O:4])=[O:3].C[Si]([C:31]#[CH:32])(C)C.C(OCC)(=O)C.CCCCCC.C(=O)([O-])[O-].[K+].[K+]>C(N(CC)CC)C.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([C:31]#[CH:32])=[CH:18][CH:17]=3)=[CH:14][C:13]([C:23]([F:26])([F:25])[F:24])=[N:12]2)=[N:9][CH:10]=1)(=[O:4])=[O:3]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 66111TrimethylsilylacetyleneHCID 99114082-[5-(4-Bromo-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methanesulfonyl-pyridineHCID 21226206Ethyl acetate hexane

Product 1

HCID 102004535-Methylsulfonyl-2-[5-(4-acetylenyl-phenyl)-3-trifluoromethyl-1h-pyrazol-1-yl]pyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

5-Methylsulfonyl-2-[5-(4-bromophenyl)-3-trifluoromethyl-1H-pyrazol-1-yl]pyridine (230 mg), Cul (5 mg), Pd(PPh3)4 (30 mg) were mixed in triethylamine (2.5 mL), followed by the addition of trimethylsilyl acetylene (0.182 mL), and the reaction mixture was heated at 80° C. for 2 hours. TLC in 1:1 of ethyl acetate/hexane showed complete conversion of the starting material to the product. The solvent was removed in vacuo to give the crude product. This crude material was then dissolved in methanol (2.5 mL), followed by the addition of potassium carbonate (20 mg). The reaction mixture was stirred at room temperature for 30 minutes. After filtration, the solvent was removed in vacuo to give the crude product which was purified by flash chromatography using 70:30 of methylene chloride/hexane to give the title compound (41 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. customto give the crude product
  3. filtrationAfter filtration
  4. customthe solvent was removed in vacuo
  5. customto give the crude product which
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-931cdfa55cc94e0abc5cd70cac543923
Source dataset
uspto-grants-2003_01
Patent number
US06506779B1

Reaction notes

Loading…