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

HRID 2423065ノート

反応式

HRID 2423065 の反応式
[Br:1][C:2]1[CH:10]=[C:9]([C:11]#[N: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]([C:11]#[N: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 247289174-Bromo-1H-indazole-6-carbonitrile

生成物 1

HCID 672446504-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazole-6-carbonitrile収率 40.7%

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-6-carbonitrile (1.0 g, 4.50 mmol) in dichloromethane (80 mL) was added 4-benzyloxy-3-fluorobenzeneboronic acid (2.2 g, 8.94 mmol), pyridine (0.71 mL, 8.78 mmol), copper acetate (1.2 g, 6.63 mmol) and powdered 4A molecular sieves (2.0 g). The reaction mixture was stirred at room temperature in the presence of air for 6 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 5-100% dichloromethane in hexane to yield the title compound (D5) (774 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 5-100% dichloromethane in hexane

出典と根拠

ORDレコード
ord-76b0cd1995504074816d4eaaf6399448
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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