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1,4-Dioxane → [6-[2-[Methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoylamino]-2-[2-tri(propan-2-yl)silylethynyl]pyridin-3-yl]boronic acid

HRID 535394
ノート
印刷プレビュー

反応式

HRID 535394 の反応式
[C:1]([O:5][C:6](=[O:33])[N:7]([CH:9]([CH3:32])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16](Br)=[C:15]([C:20]#[C:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[N:14]=1)=[O:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[B:34]1(B2OCC(C)(C)CO2)[O:39]CC(C)(C)C[O:35]1.CC([O-])=O.[K+].O1CCOCC1>C(Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[CH3:8][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:33])[CH:9]([CH3:32])[C:10]([NH:12][C:13]1[N:14]=[C:15]([C:20]#[C:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[C:16]([B:34]([OH:39])[OH:35])=[CH:17][CH:18]=1)=[O:11]
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 312751,4-DioxaneHCID 517044Potassium AcetateHCID 2734316Bis(neopentyl glycolato)diboronHCID 86694383Tert-butyl (1-((5-bromo-6-((triisopropylsilyl)ethynyl)pyridin-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate

生成物 1

HCID 86694386[6-[2-[Methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoylamino]-2-[2-tri(propan-2-yl)silylethynyl]pyridin-3-yl]boronic acid

試薬・触媒・溶媒 3

HCID 24290Palladium Chloride触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

A mixture of tert-butyl-N-[1-[[5-bromo-6-[2-tri(propan-2-yl)silylethynyl]pyridin-2-yl]-amino]-1-oxopropan-2-yl]-N-methylcarbamate C1a (51 g, 90 mmol), bis(neopentyl glycolato)diboron (40.5 g, 179 mmol), KOAc (26.4 g, 269 mmol), 1,1′-Bis(diphenyl-phosphino)ferrocene]dichloropalladium(II) (3.3 g, 4.5 mmol) and dioxane (400 ml) is stirred under argon atmosphere for 17 h at 50° C. The mixture is diluted with DCM and extracted with a saturated aqueous solution of NaHCO3. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by NP chromatography. Yield: 21.9 g (48%). HPLC-MS: M+H=504; tR=2.17 min (*Method—4).

後処理

  1. extractionextracted with a saturated aqueous solution of NaHCO3
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by NP chromatography

出典と根拠

ORDレコード
ord-f5bf572391fd483a8da230d5a5d9f996
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08859541B2

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