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

HRID 1789858
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HRID 1789858 반응식
[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]
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참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매2회

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온도
0 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-184708061ceb4f5cb122024729392cba
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07071175B1

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