Chloride → HCID 67313333, compound

HRID 1391503Notes

Reaction equation

HRID 1391503 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12](Cl)=[N:13][OH:14].[Cl:16][C:17]1[CH:18]=[C:19]([C:23]#[C:24][C:25]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:26])[CH:20]=[CH:21][CH:22]=1.N1C=CC=C(C=O)C=1.I(C1C=CC=CC=1C(O)=O)=O.C(=O)(O)[O-].[Na+].[Cl-]>C(O)(C)C.CCOCC>[Cl:16][C:17]1[CH:18]=[C:19]([C:23]2[O:14][N:13]=[C:12]([C:3]3[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=3[F:1])[C:24]=2[C:25]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:26])[CH:20]=[CH:21][CH:22]=1

Participants

9

Reactant 6

HCID 312ChlorideHCID 103713-PyridinecarboxaldehydeHCID 675372-Iodosylbenzoic acidHCID 516892Sodium Bicarbonate2×HCID 67314987HCID 67314987, compoundHCID 86229620HCID 86229620, compound

Product 1

HCID 67313333HCID 67313333, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 60 mg (0.25 mmol) of 2-fluoro-5-trifluoromethyl-N-hydroxybenzenecarbox-imidoyl chloride, 50 mg (0.21 mmol) of 3-(3-chlorophenyl) 1-(3-pyridyl)-2-propyn-1-one (prepared similarly to procedures noted above from lithio 3-chlorophenylacetylide and 3-pyridinecarboxaldehyde, followed by IBX oxidation), and 26 mg (0.36 mmol) of sodium bicarbonate in 2.5 mL of isopropyl alcohol was heated at 55° C. overnight with shaking. An additional 30 mg of carboximidoyl chloride and 15 mg of sodium bicarbonate were added, and the reaction was heated for another 24 hrs. The mixture was cooled and diluted with ether. The ether fraction was washed with saturated sodium chloride and dried over magnesium sulfate. The drying agent was filtered off, and solvent was removed by rotoevaporation. The residue was purified by prepTLC to give 56 mg (0.13 mmol) of 5-(3-chlorophenyl)-3-(2-fluoro-5-trifluoromethylphenyl)-4-[(3-pyridyl)carbonyl]isoxazole. 1H NMR (CDCl3): δ 7.10 (t, 1), 7.41 (m, 1), 7.52 (m, 1), 8.65 (br s, 1), and 8.86 ppm (br s, 1). MS m/z: 447.0 (M+H).

Workup

  1. customprepared similarly to procedures
  2. temperaturethe reaction was heated for another 24 hrs
  3. temperatureThe mixture was cooled
  4. washThe ether fraction was washed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe drying agent was filtered off
  7. customsolvent was removed by rotoevaporation
  8. customThe residue was purified by prepTLC

Sources & evidence

ORD record
ord-420bf446d4cd41a7b3041f02eca8540c
Source dataset
uspto-grants-2008_03
Patent number
US07338967B2

Reaction notes

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