1,2-Dichloroethane → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylpyridin

HRID 1789834노트

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HRID 1789834 반응식
[C:1]([O:5][C:6]([N:8]([C:16]1[CH:21]=[C:20]([CH3:22])[C:19](Br)=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]([Si:28](C)(C)OC[Sn](CCCC)(CCCC)CCCC)([CH3:27])([CH3:26])[CH3:25].C([O:48][CH2:49][CH3:50])C.[F-].[K+].Cl[CH2:54]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]([N:8]([C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([C:49]([CH3:50])([CH3:54])[O:48][SiH2:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 3283Diethyl EtherHCID 522689Potassium FluorideHCID 14270862Tert-butyl-dimethyl-(tributylstannylmethoxy)silaneHCID 220360532-[N,N-Bis(tert-butoxycarbonyl)amino]-5-bromo-4-methylpyridine

생성물 1

HCID 1317258282-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylpyridin수율 57%

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매

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온도
0 °C

실험 절차

A solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromo-4-methylpyridin (15.0 g, 38.70 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (25.4 g, 58.3 mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.90 g, 1.42 mmol) in 1,2dichloroethane (50 mL) was stirred at 90° C. for two days. The mixture was cooled to 0° C. and diethyl ether (200 mL) was added followed by saturated aqueous potassium fluoride (40 mL). The mixture was stirred vigourously for 30 min and filtered. The organic phase was washed with water, dried and concentrated under reduced pressure. Flash chromatography (hexane/EtOAc, 95:5) gave 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylpyridin (10.0 g, 57%).

후처리

  1. filtrationfiltered
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-11b564af92244385904b20e883187645
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071175B1

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