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

HRID 539055ノート

反応式

HRID 539055 の反応式
Cl[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=4)[CH2:14][O:13][C:12]3=[O:22])=[N:7][C:6]=12.C(=O)([O-])[O-].[Na+].[Na+].[F:29][C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:32][C:31]=1[C:45]1[N:49]=[CH:48][N:47]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[N:46]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>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>[F:29][C:30]1[CH:35]=[C:34]([C:2]2[CH:3]=[N:4][N:5]3[CH:10]=[CH:9][C:8]([N:11]4[CH:15]([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=5)[CH2:14][O:13][C:12]4=[O:22])=[N:7][C:6]=23)[CH:33]=[CH:32][C:31]=1[C:45]1[N:49]=[CH:48][N:47]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[N:46]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67034012HCID 67034012、化合物HCID 670346473-(3-Chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one

生成物 1

HCID 670347823-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one収率 48.5%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a solution of 3-(3-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one (0.42 g, 1.3 mmol) in dioxanes was added sodium carbonate solution (2.0 M, 3.3 ml, 6.7 mmol) and 3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole (0.61 g, 1.5 mmol) and the reaction bubbled with nitrogen for 30 minutes, followed by the addition of XPHOS (0.63 g, 1.3 mmol) and Pd2 dba3 (1.2 g, 1.3 mmol), and the reaction stirred at 80° C. for 3 hours. The reaction was poured into water and extracted into EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by normal phase chromatography using a gradient eluent from 25% EtOAc in hexane to EtOAc to yield 3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one (0.36 g, 0.63 mmol, 47% yield).

後処理

  1. customthe reaction bubbled with nitrogen for 30 minutes
  2. extractionextracted into EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by normal phase chromatography

出典と根拠

ORDレコード
ord-26f21f4f38be4c47adc23c0261405edc
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

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