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Potassium Phosphate, Tribasic → N-(4-tert-butyl-benzyl)-3-chloro-5-ethyl-N-[2-(3-fluoro-5-trifluoromethyl-phenyl)-ethyl]-benzamide

HRID 19811
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HRID 19811 반응식
Br[C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([Cl:35])[CH:34]=1)[C:5]([N:7]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([F:20])[CH:11]=1)=[O:6].[CH2:36](B(O)O)[CH3:37].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([CH2:21][N:7]([CH2:8][CH2:9][C:10]2[CH:15]=[C:14]([C:16]([F:18])([F:17])[F:19])[CH:13]=[C:12]([F:20])[CH:11]=2)[C:5](=[O:6])[C:4]2[CH:3]=[C:2]([CH2:36][CH3:37])[CH:34]=[C:33]([Cl:35])[CH:32]=2)=[CH:23][CH:24]=1)([CH3:30])([CH3:29])[CH3:31]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 521157Ethylboronic acidHCID 866139943-bromo-N-(4-tert-butyl-benzyl)-5-chloro-N-[2-(3-fluoro-5-trifluoromethyl-phenyl)-ethyl]-benzamide

생성물 1

HCID 68563631N-(4-tert-butyl-benzyl)-3-chloro-5-ethyl-N-[2-(3-fluoro-5-trifluoromethyl-phenyl)-ethyl]-benzamide수율 61.5%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회HCID 1140Toluene용매

실험 절차

285 mg of 3-bromo-N-(4-tert-butyl-benzyl)-5-chloro-N-[2-(3-fluoro-5-trifluoromethyl-phenyl)-ethyl]-benzamide (0.6 mmol, Example B177), 44 mg of ethylboronic acid (1.75 mmol), 371 mg of tri-potassium phosphate (0.05 mmol), 14 mg of tricyclohexylphosphine and 6 mg of palladium acetate were suspended in 2.3 ml toluene and 0.1 ml water and stirred at 100° C. for 3.5 h under nitrogen. The reaction mixture was then cooled down to RT, diluted with 4 ml water and extracted twice with ethylacetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered off and concentrated under vacuo. The resulting residue was purified by flash column chromatography (Heptane/AcOEt:95/5) to yield 192 mg of a yellow solid. MS (ISP) 520.3 (M+H)+.

후처리

  1. extractionextracted twice with ethylacetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered off
  5. concentrationconcentrated under vacuo
  6. customThe resulting residue was purified by flash column chromatography (Heptane/AcOEt:95/5)

출처 및 근거

ORD 기록
ord-d21cfe3388354277955c93e18fae43b7
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745477B2

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