2-Fluoro-4-nitrophenol → 7-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[3,2-b]pyridine

HRID 1711041노트

반응식

HRID 1711041 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][NH:10][C:3]=12.[F:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[OH:21].C([O-])([O-])=O.[K+].[K+]>O(C1C=CC=CC=1)C1C=CC=CC=1>[F:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[O:21][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][NH:10][C:3]=12

참가 물질

5

반응물 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 224762367-Chloro-1H-pyrrolo[3,2-b]pyridine

생성물 1

HCID 594245967-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[3,2-b]pyridine수율 26.1%

시약·촉매·용매 1

HCID 7583Diphenyl Ether용매

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온도
170 °C

실험 절차

A mixture of 266 (180 mg, 1.18 mmol), 2-fluoro-4-nitrophenol (558 mg, 3.55 mmol) and K2CO3(981 mg, 7.10 mmol) in Ph2O (4 mL) was heated at 170° C. for 8 hours, cooled to room temperature and partitioned between EtOAc and water. Organic phase was collected, dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash column chromatography with gradient elution of hexane, to hexane/EtOAc (1:1), to afford the title compound 267 (84 mg, 26% yield) as a yellowish solid. MS (m/z): 274. 1 (M+H) (found).

후처리

  1. temperaturecooled to room temperature
  2. custompartitioned between EtOAc and water
  3. customOrganic phase was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography with gradient elution of hexane, to hexane/EtOAc (1:1)

출처 및 근거

ORD 기록
ord-27113b4ced774d86ad8e1ba7fbd4eb33
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790729B2

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