Pyridine → 4-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazole

HRID 2423092ノート

反応式

HRID 2423092 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][C:20]=1[F:28])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:20]([F:28])[CH:21]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 223525484-bromo-1H-indazole

生成物 1

HCID 592729654-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazole収率 60.3%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-bromo-1H-indazole (4.32 g, 21.9 mmol) in dichloromethane (100 mL) was added 4-benzyloxy-3-fluorobenzeneboronic acid (10.8 g, 43.9 mmol), pyridine (3.5 mL, 43.3 mmol), copper acetate (5.9 g, 32.6 mmol) and powdered 4A molecular sieves (5 g). The reaction mixture was stirred at room temperature in the presence of air for 5 days. Celite was added to the reaction mixture and the mixture stirred for 5 minutes. The mixture was then filtered through a pad of celite and washed with dichloromethane and then the filtrate concentrated in vacuo. The residue was diluted in dichloromethane and water. After separation of the layers, the aqueous phase was extracted with dichloromethane (×4). The combined organic layers were dried over magnesium sulphate, filtered and concentrated in vacuo. The product was purified by silica gel chromatography eluting with 10-80% dichloromethane in hexane to yield the title compound (D38) (5.25 g).

後処理

  1. additionCelite was added to the reaction mixture
  2. stirringthe mixture stirred for 5 minutes
  3. filtrationThe mixture was then filtered through a pad of celite
  4. washwashed with dichloromethane
  5. concentrationthe filtrate concentrated in vacuo
  6. additionThe residue was diluted in dichloromethane
  7. customAfter separation of the layers
  8. extractionthe aqueous phase was extracted with dichloromethane (×4)
  9. dry with materialThe combined organic layers were dried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe product was purified by silica gel chromatography
  13. washeluting with 10-80% dichloromethane in hexane

出典と根拠

ORDレコード
ord-db61be125077400f86793ce70cef133e
出典データセット
uspto-grants-2011_06
特許番号
US07960563B2

反応ノート

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