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Cesium carbonate → Methyl 3-[[5-[3-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate

HRID 1427098
ノート
印刷プレビュー

反応式

HRID 1427098 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1[C:11]([CH3:21])=[C:12]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:13]([O:15][CH3:16])=[O:14])=[O:8].[C:24]([Si:28]([CH3:37])([CH3:36])[O:29][CH:30]1[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]1)([CH3:27])([CH3:26])[CH3:25].C([O-])([O-])=O.[Cs+].[Cs+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>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]>[Si:28]([O:29][CH:30]1[CH2:35][CH2:34][CH2:33][N:32]([C:2]2[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([CH:22]=2)[C:7]([NH:9][C:10]2[C:11]([CH3:21])=[C:12]([CH:17]=[CH:18][C:19]=2[CH3:20])[C:13]([O:15][CH3:16])=[O:14])=[O:8])[CH2:31]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:37])[CH3:36]
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 10796Cesium carbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 223524143-((Tert-butyldimethylsilyl)oxy)piperidineHCID 86707319Methyl 3-[(5-bromo-2-methyl-benzoyl)amino]-2,4-dimethyl-benzoate

生成物 1

HCID 86707330Methyl 3-[[5-[3-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate
収率 60%

試薬・触媒・溶媒 2

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

反応条件

温度
100 °C

実験手順

To a solution of methyl 3-[(5-bromo-2-methyl-benzoyl)amino]-2,4-dimethyl-benzoate (0.5 g, 1.32 mmol), tert-butyl-dimethyl-(3-piperidyloxy)silane (0.425 g, 1.98 mmol) and Cs2CO3 (1.28 g, 3.96 mmol) in 1,4-dioxane (15 ml) is added Pd2(dba)3 (0.12 g, 0.132 mmol) followed by S-Phos (0.054 g, 0.132 mmol). The reaction mixture is purged with nitrogen for 5 minutes and then heated at 100° C. After 16 hours, the reaction is cooled to ambient temperature, filtered through Celite™, and washed with EtOAc. The combined filtrates are dried over sodium sulfate, filtered, and concentrated under reduced pressure and purified by flash chromatography (silica gel) using 10% EtOAc in hexane to afford the title compound as a brown semi-solid (0.4 g, 60%).

後処理

  1. customThe reaction mixture is purged with nitrogen for 5 minutes
  2. temperaturethe reaction is cooled to ambient temperature
  3. filtrationfiltered through Celite™
  4. washwashed with EtOAc
  5. dry with materialThe combined filtrates are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified by flash chromatography (silica gel)

出典と根拠

ORDレコード
ord-87170ceb8522402eb17ac37fe6d55a7a
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933098B2

反応ノート

読み込み中…

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