Potassium Carbonate → 2-Pyridinyl 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylate

HRID 383224ノート

反応式

HRID 383224 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:27]([F:30])([F:29])[F:28])[O:13][N:12]=[C:11]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([C:24]([OH:26])=[O:25])=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(Cl)(=O)C(Cl)=O.O[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1.C([O-])([O-])=O.[K+].[K+]>ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:27]([F:28])([F:30])[F:29])[O:13][N:12]=[C:11]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([C:24]([O:26][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=4)=[O:25])=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 583386304-[5-(3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylic acidHCID 178516071HCID 178516071、化合物

生成物 1

HCID 685124832-Pyridinyl 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylate収率 46%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred suspension of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylic acid (prepared according to the procedure described in WO 2007/079162, 1.50 g, 3.30 mmol) in dichloromethane (15 mL) at room temperature was added oxalyl chloride (0.58 mL, 6.60 mmol) followed by one drop of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 2 h and then concentrated under vacuum. The residue was dissolved in dichloromethane (10 mL) and added to a stirred suspension of 2-hydroxypyridine (0.38 g, 3.96 mmol) and K2CO3 (1.37 g, 9.90 mmol) in dichloromethane (15 mL) at room temperature. The resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered through a short pad of Celite® diatomaceous filter aid, and the pad was rinsed with dichloromethane. The combined filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/EtOAc as eluent to provide the title product as a yellow solid (0.80 g, 46% yield).

後処理

  1. customprepared
  2. customat room temperature
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in dichloromethane (10 mL)
  5. customThe resulting reaction mixture
  6. stirringwas stirred at room temperature overnight
  7. filtrationThe reaction mixture was filtered through a short pad of Celite® diatomaceous filter aid
  8. washthe pad was rinsed with dichloromethane
  9. concentrationThe combined filtrate was concentrated
  10. customthe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-c35ce055db994dbca3abd04216ff14cc
出典データセット
uspto-grants-2013_02
特許番号
US08367584B2

反応ノート

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