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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
ノート
印刷プレビュー

反応式

HRID 539050 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 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
収率 74%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cccb3dbe7ef74972b243faf143ca6a8e
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08865726B2

反応ノート

読み込み中…

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