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

HRID 890465

반응식

HRID 890465 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8a7206d3d114428ebd1a9fdc3e993cb6
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995263B2

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