Pyridine → 3-Bromo-1-(tert-butyl-dimethyl-silanyl)-5-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridine

HRID 1024397노트

반응식

HRID 1024397 반응식
[Br:1]Br.[C:3]([Si:7]([CH3:24])([CH3:23])[N:8]1[C:12]2=[N:13][CH:14]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:16]=[C:11]2[CH:10]=[CH:9]1)([CH3:6])([CH3:5])[CH3:4].N1C=CC=CC=1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[Br:1][C:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:16]=2)[N:8]([Si:7]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:24])[CH3:23])[CH:9]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 24408BromineHCID 22607107sodium thiosulfate NaHCO3HCID 575980361-(tert-Butyl-dimethyl-silanyl)-5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 575980783-Bromo-1-(tert-butyl-dimethyl-silanyl)-5-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridine수율 78%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 6212Chloroform용매

반응 조건

온도
0 °C

실험 절차

A solution of bromine (0.166 mL, 0.0032 mol) in 1 mL of CCl4 was added dropwise to a stirred solution of 20 (1.0 g, 0.0032 mol) and pyridine (0.314 mL, 0.0039 mol) in dry CHCl3 (30 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and then neutralized with 10 mL of a mixture of sodium bicarbonate-sodium thiosulfate (1:1). The organic layer was separated and further extracted with dichloromethane (3×10 mL) and the combined organics dried and concentrated in vacuo. The residue was subjected to flash chromatography (30% EtOAc-70% hexanes) to give 0.97 g (78%) of the desired material 21. 1H NMR CDCl3 8.9 (s, 1H), 8.55 (d, 1H), 8.4 (d, 1H), 8.0 (d, 1H), 7.9 (d, 1H), 7.4 (dd, 1H), 7.2 (s, 1H), 0.9 (s, 9H), 0.5 (s, 6H).

후처리

  1. customThe organic layer was separated
  2. extractionfurther extracted with dichloromethane (3×10 mL)
  3. customthe combined organics dried
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-18f48ceb1c3c4b77b3fcd95fcc6698e3
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722889B2

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