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Water → Methyl 2-(4-(4'-(2-methyl-5-(trifluoromethyl)oxazole-4-carboxamido)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

HRID 881733
ノート
印刷プレビュー

反応式

HRID 881733 の反応式
[CH3:1][C:2]1[O:3][C:4]([C:25]([F:28])([F:27])[F:26])=[C:5]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13](B3OC(C)(C)C(C)(C)O3)=[CH:12][CH:11]=2)=[O:8])[N:6]=1.Br[C:30]1[CH:35]=[CH:34][C:33]([C:36]23[CH2:43][CH2:42][C:39]([CH2:44][C:45]([O:47][CH3:48])=[O:46])([CH2:40][CH2:41]2)[O:38][CH2:37]3)=[CH:32][CH:31]=1.O.[F-].[Cs+]>O1CCOCC1.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH3:1][C:2]1[O:3][C:4]([C:25]([F:26])([F:27])[F:28])=[C:5]([C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([C:30]3[CH:31]=[CH:32][C:33]([C:36]45[CH2:41][CH2:40][C:39]([CH2:44][C:45]([O:47][CH3:48])=[O:46])([CH2:42][CH2:43]4)[O:38][CH2:37]5)=[CH:34][CH:35]=3)=[CH:14][CH:15]=2)=[O:8])[N:6]=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

7

反応物 4

HCID 962WaterHCID 25953Cesium fluorideHCID 86700823Methyl 2-(4-(4-bromophenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetateHCID 867008372-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(trifluoromethyl)oxazole-4-carboxamide

生成物 1

HCID 86700838Methyl 2-(4-(4'-(2-methyl-5-(trifluoromethyl)oxazole-4-carboxamido)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate
収率 50%

試薬・触媒・溶媒 2

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a mixture of 2-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(trifluoromethyl)oxazole-4-carboxamide (300 mg, 0.757 mmol) and methyl 2-(4-(4-bromophenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (257 mg, 0.757 mmol) in dioxane (3 ml) was added H2O (0.33 ml) at room temperature. CsF (345 mg, 2.272 mmol) and Pd(amphos)Cl2 (53.6 mg, 0.076 mmol) were added and the mixture was degassed several times before being heated to 90° C. for overnight. The reaction mixture was cooled to room temperature and directly purified by column chromatography to afford the title compound as white solid after drying (200 mg, 50% yield). LC/MS, ESI-MS(+): 529.0, RT: 1.52 (Condition E).

後処理

  1. customthe mixture was degassed several times
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customdirectly purified by column chromatography

出典と根拠

ORDレコード
ord-64412e2ef876479b88d45b5caf1b701a
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08993619B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート