Chloride → HCID 67313333、化合物

HRID 1010702ノート

反応式

HRID 1010702 の反応式
[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

参加物

9

反応物 6

HCID 312ChlorideHCID 103713-PyridinecarboxaldehydeHCID 675372-Iodosylbenzoic acidHCID 516892Sodium Bicarbonate2 回HCID 67314987HCID 67314987、化合物HCID 86229620HCID 86229620、化合物

生成物 1

HCID 67313333HCID 67313333、化合物収率 61.9%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 3776Isopropanol溶媒

反応条件

温度
55 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8297fecd97474d44b1e006ce294edba7
出典データセット
uspto-grants-2011_07
特許番号
US07977341B2

反応ノート

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