Chloride → HCID 67313333, 화합물

HRID 1010702노트

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HRID 1010702 반응식
[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

참가 물질

9

반응물 6

HCID 312ChlorideHCID 103713-PyridinecarboxaldehydeHCID 675372-Iodosylbenzoic acidHCID 516892Sodium Bicarbonate2회HCID 67314987HCID 67314987, 화합물HCID 86229620HCID 86229620, 화합물

생성물 1

HCID 67313333HCID 67313333, 화합물수율 61.9%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 3776Isopropanol용매

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온도
55 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8297fecd97474d44b1e006ce294edba7
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977341B2

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