Potassium Phosphate, Tribasic → HCID 16063512, 화합물

HRID 1993926노트

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HRID 1993926 반응식
Br[C:2]1[C:3](=[O:24])[N:4]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[N:5]([CH3:16])[C:6]=1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1.[CH:25]1(B(O)O)[CH2:27][CH2:26]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH:25]1([C:2]2[C:3](=[O:24])[N:4]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[N:5]([CH3:16])[C:6]=2[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH2:27][CH2:26]1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 686775324-Bromo-2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one

생성물 1

HCID 16063512HCID 16063512, 화합물수율 19.6%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매HCID 22728543Water ethylacetate용매

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온도
100 °C

실험 절차

Into a sealable tube under argon was added 4-bromo-2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one (0.312 g), cyclopropylboronic acid (0.139 g), potassium phosphate (0.924 g), tricyclohexyl phosphine (0.034 g) and toluene (3.0 mL). To this was added palladium acetate (0.013 g) and the tube was sealed and stirred at 100° C. for 20 hours. The reaction vessel was then cooled and the diluted with water/EtOAc. The phases were separated and the aqueous phase was extracted with further EtOAc. The combined organic phases were washed with brine, dried over sodium sulfate and evaporated in vacuo to afford a crude residue. Flash column chromatography over silica gel using ISCO combiflash chromatography and eluting with EtOAc/heptane afforded the desired 4-cyclopropyl-2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one (0.055 g) as a white crystalline solid. MS (ESI+): 315.1 ([M+H]+).

후처리

  1. customthe tube was sealed
  2. temperatureThe reaction vessel was then cooled
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with further EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customto afford a crude residue
  9. washFlash column chromatography over silica gel using ISCO combiflash chromatography and eluting with EtOAc/heptane

출처 및 근거

ORD 기록
ord-10f73f28b734455d811820ab9c4362b1
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652057B2

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