Potassium Phosphate, Tribasic → 3-Pyridinecarboxylic acid,4-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]-,methyl ester

HRID 890465

反応式

HRID 890465 の反応式
Cl[C:2]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:9][O:8][C:6](=[O:7])[C:5]1[C:10]([C:12]([F:15])([F:14])[F:13])=[CH:11][C:2]([C:21]2[CH:22]=[CH:23][C:18]([C:17]([F:28])([F:27])[F:16])=[CH:19][CH:20]=2)=[N:3][CH:4]=1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 2775340Methyl 6-chloro-4-(trifluoromethyl)nicotinate

生成物 1

HCID 768528783-Pyridinecarboxylic acid,4-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]-,methyl ester収率 71%

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

To a solution of bis(triphenylphosphine)palladium(II)chloride (0.84 g, 1.2 mmol), methyl 6-chloro-4-(trifluoromethyl)nicotinate (9.58 g, 40 mmol) and 4-(trifluoromethyl) benzene boronic acid (10.1 g, 52 mmol) in degassed toluene (200 ml) was added aqueous 2 M K3PO4 (40 ml). The suspension was stirred at 80° C. for 16 h. The reaction mixture was cooled to RT, ice water was added and the mixture was extracted three times with diethyl ether. The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated. Purification by flash-chromatography on silica gel (dichloromethane/heptane 2:1 to 1:1) gave 9.91 g (28.3 mmol, 71%) of the title compound as off-white powder.

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionthe mixture was extracted three times with diethyl ether
  3. washThe organic phases were washed with aqueous 10% NaCl
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customPurification by flash-chromatography on silica gel (dichloromethane/heptane 2:1 to 1:1)

出典と根拠

ORDレコード
ord-8a7206d3d114428ebd1a9fdc3e993cb6
出典データセット
uspto-grants-2006_02
特許番号
US06995263B2

関連ノート

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