Pyridine → 4-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-6-(methyloxy)-1H-indazole

HRID 2423063ノート

反応式

HRID 2423063 の反応式
[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][C:22]=1[F:30])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:22]([F:30])[CH:23]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 247283154-Bromo-6-methoxy-1H-indazole

生成物 1

HCID 592729754-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-6-(methyloxy)-1H-indazole収率 46.8%

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-6-(methyloxy)-1H-indazole (200 mg, 0.88 mmol) in dichloromethane (10 mL) was added 4-benzyloxy-3-fluorobenzeneboronic acid (433 mg, 1.76 mmol), pyridine (0.14 mL, 1.73 mmol), copper acetate (239 mg, 1.32 mmol) and powdered 4A molecular sieves (500 mg). The reaction mixture was stirred at room temperature in the presence of air for 3 days. Celite was added to the mixture then the mixture was filtered through a pad of celite and then the filtrate concentrated in vacuo. The product was purified by silica gel chromatography eluting with 5-80% dichloromethane in hexane to yield the title compound (D3) (176 mg).

後処理

  1. additionCelite was added to the mixture
  2. filtrationthe mixture was filtered through a pad of celite
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe product was purified by silica gel chromatography
  5. washeluting with 5-80% dichloromethane in hexane

出典と根拠

ORDレコード
ord-186f6d111265434983dbd673367d7557
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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