5-Fluorogramine → 5-fluoro-3-(2-pyridin-3-yl-vinyl)-1H-indole

HRID 2382045노트

반응식

HRID 2382045 반응식
CN([CH2:4][C:5]1[C:9]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]=2[NH:7][CH:6]=1)C.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=O)[CH:16]=1.P(CCCC)(CCCC)CCCC>CC#N>[F:14][C:11]1[CH:10]=[C:9]2[C:8](=[CH:13][CH:12]=1)[NH:7][CH:6]=[C:5]2[CH:4]=[CH:21][C:17]1[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 95765-FluorogramineHCID 103713-PyridinecarboxaldehydeHCID 13831Tributylphosphine

생성물 1

HCID 685566735-fluoro-3-(2-pyridin-3-yl-vinyl)-1H-indole

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
90 °C

실험 절차

A solution of 5-fluorogramine (576 mg, 3 mmol) and pyridine-3-carboxaldehyde (531 mg, 3 mmol) in MeCN (6 mL) is treated with Bu3P (1.12 mL, 4.5 mmol) and stirred at 90° C. for 24 h. The mixture is concentrated, filtered through a pad of silica gel eluting with 30% EtOAc in heptane to afford 5-fluoro-3-(2-pyridin-3-yl-vinyl)-1H-indole as a mixture of olefin isomers, which is used in the next step without further purification.

후처리

  1. concentrationThe mixture is concentrated
  2. filtrationfiltered through a pad of silica gel eluting with 30% EtOAc in heptane

출처 및 근거

ORD 기록
ord-5eec87a0265840689371f9cedbba3d80
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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