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Sodium Carbonate → (S)-4-phenyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one

HRID 539050
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HRID 539050 반응식
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[C@@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:14][O:13][C:12]3=[O:22])=[N:7][C:6]=12.C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:37]2[CH:42]=[CH:41][C:40]([C:43]3[N:47]=[CH:46][N:45]([CH2:48][O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])[N:44]=3)=[CH:39][CH:38]=2)O1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:16]1([C@H:15]2[CH2:14][O:13][C:12](=[O:22])[N:11]2[C:8]2[CH:9]=[CH:10][N:5]3[N:4]=[CH:3][C:2]([C:37]4[CH:38]=[CH:39][C:40]([C:43]5[N:47]=[CH:46][N:45]([CH2:48][O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])[N:44]=5)=[CH:41][CH:42]=4)=[C:6]3[N:7]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
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참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 595255703-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazoleHCID 67034277(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-phenyloxazolidin-2-one

생성물 1

HCID 67034450
(S)-4-phenyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one
수율 74%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To a solution of (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-phenyloxazolidin-2-one (0.7 g, 1.9 mmol) in dioxane bubbled with nitrogen was added sodium carbonate (2.0 M, 4.9 mL, 9.7 mmol) and 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole (1.0 g, 2.5 mmol), and the reaction was degassed with nitrogen for 30 minutes. XPHOS (0.093 g, 0.19 mmol) and Pd2 dba3 (0.089 g, 0.097 mmol) were added to the mixture and the reaction was stirred for 2 hours at 80° C. The reaction was poured into water and the aqueous layer extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material purified by normal phase chromatography using 25% EtOAc/DCM as the eluent to yield (S)-4-phenyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (0.80 g, 1.4 mmol, 74% yield).

후처리

  1. customthe reaction was degassed with nitrogen for 30 minutes
  2. extractionthe aqueous layer extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material purified by normal phase chromatography

출처 및 근거

ORD 기록
ord-cccb3dbe7ef74972b243faf143ca6a8e
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08865726B2

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