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1,2-Dichloroethane → tert-butyl N-[5-(2-tert-butylsilyloxypropan-2-yl)-6-methyl-2-pyridinyl]carbamate

HRID 1789858
ノート
印刷プレビュー

反応式

HRID 1789858 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[C:10]([CH3:15])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:17]([Si:21](C)(C)OC[Sn](CCCC)(CCCC)CCCC)([CH3:20])([CH3:19])[CH3:18].C([O:41][CH2:42][CH3:43])C.[F-].[K+].Cl[CH2:47]CCl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:42]([CH3:43])([CH3:47])[O:41][SiH2:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:10]([CH3:15])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]
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 5

HCID 111,2-DichloroethaneHCID 3283Diethyl EtherHCID 522689Potassium FluorideHCID 14270862Tert-butyl-dimethyl-(tributylstannylmethoxy)silaneHCID 54039100tert-Butyl (5-bromo-6-methylpyridin-2-yl)carbamate

生成物 1

HCID 131725830tert-butyl N-[5-(2-tert-butylsilyloxypropan-2-yl)-6-methyl-2-pyridinyl]carbamate
収率 47%

試薬・触媒・溶媒 1

HCID 178418476HCID 178418476、化合物触媒2 回

反応条件

温度
0 °C

実験手順

A solution of (5-bromo-6-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester (27.5 g, 95.8 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (43.5 g, 100.2 mmol), and bis(triphenylphosphine)palladium(II) dichloride (1.00 g, 1.40 mmol) in 1,2-dichloroethane (350 mL) was stirred at reflux for 48 h. Additional bis(triphenylphosphine)palladium(II) dichloride (1.00 g, 1.40 mmol) was added every 12 h. The mixture was cooled to 0° C. and diethyl ether (300 mL) was added followed by saturated aqueous potassium fluoride (100 mL). The mixture was stirred vigourously for 60 min and filtered. The organic phase was washed with water, dried and concentrated under reduced pressure. Flash chromatography (MeOH/CH2Cl2, 1:99) gave [5-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-pyridin-2-yl]-carbamic acid tert-butyl ester (15 g, 47%).

後処理

  1. temperatureat reflux for 48 h
  2. filtrationfiltered
  3. washThe organic phase was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-184708061ceb4f5cb122024729392cba
出典データセット
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07071175B1

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