Sodium hydride → 7-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine

HRID 246481

반응식

HRID 246481 반응식
[Br:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.[H-].[Na+].Cl[CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[Br:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:7]=12

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 196964567-Bromo-6-azaindole

생성물 1

HCID 866779827-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

To a stirred solution of 7-bromo-1H-pyrrolo[2,3-c]pyridine (0.2 g, 1.02 mmol) in DMF (5 mL), cooled to 0° C., was added sodium hydride (46.7 mg, 1.17 mmol). After 10 min the mixture was warmed to 25° C. After 20 min the mixture was recooled to 0° C. and (2-(chloromethoxy)ethyl)trimethylsilane (186 mg, 1.12 mmol) added drop-wise. After 5 min the mixture was warmed to 25° C. After 20 min the mixture was partitioned between ethyl acetate and water. The organic phase was washed with water then concentrated in vacuo. Purification by chromatography (silica, 12 g Analogix column, 0-8% ethyl acetate in hexanes) gave 7-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine (0.28 g, 84%) as a colorless oil.

후처리

  1. temperatureAfter 5 min the mixture was warmed to 25° C
  2. customAfter 20 min the mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water
  4. concentrationthen concentrated in vacuo
  5. customPurification by chromatography (silica, 12 g Analogix column, 0-8% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-78677bea67a646aa9ba29b4b70cfdefe
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

연결된 노트

불러오는 중…