1,2-Dichloroethane → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin

HRID 1789825노트

반응식

HRID 1789825 반응식
Br[C:2]1[CH:3]=[C:4]([CH3:23])[C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[N:6][CH:7]=1.[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:12]([O:11][C:9]([N:8]([C:5]1[C:4]([CH3:23])=[CH:3][C:2]([C:49]([CH3:50])([CH3:54])[O:48][SiH2:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:7][N:6]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:10])([CH3:15])([CH3:14])[CH3:13]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 3283Diethyl EtherHCID 522689Potassium FluorideHCID 14270862Tert-butyl-dimethyl-(tributylstannylmethoxy)silaneHCID 220360402-(N,N-BisBOC-amino)-5-bromo-3-methylpyridine

생성물 1

HCID 1317258272-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin수율 59%

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매

반응 조건

온도
0 °C

실험 절차

A solution of 5-bromo-2-[N,N-bis(tert-butoxycarbonyl)amino]-3-methyl-pyridin (26.0 g, 67.1 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (47.6 g, 109 mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.90 g, 1.42 mmol) in 1,2-dichloroethane (80 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, 100:0→95:5) gave 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin (18.0 g, 59%).

후처리

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

출처 및 근거

ORD 기록
ord-36d991e903c24644903420e72332da4d
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071175B1

반응 노트

불러오는 중…