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

HRID 1711041ノート

反応式

HRID 1711041 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7583Diphenyl Ether溶媒

反応条件

温度
170 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-27113b4ced774d86ad8e1ba7fbd4eb33
出典データセット
uspto-grants-2010_09
特許番号
US07790729B2

反応ノート

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