Stannous Chloride → 6-Bromo-3-phenyl-1H-indazole

HRID 563391ノート

反応式

HRID 563391 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[N:17]([O-])=O.[Na+].[Sn](Cl)Cl>Cl>[Br:8][C:6]1[CH:7]=[C:2]2[C:3]([C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:17][NH:1]2)=[CH:4][CH:5]=1

参加物

5

反応物 3

HCID 24479Stannous ChlorideHCID 4149946(2-Amino-4-bromophenyl)(phenyl)methanoneHCID 23668193Sodium Nitrite

生成物 1

HCID 573551936-Bromo-3-phenyl-1H-indazole収率 42%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
0 °C

実験手順

To a stirred mixture of (2-amino-4-bromophenyl)(phenyl)methanone (1.0 g, 3.6 mmol) in hydrochloric acid (6N aqueous solution, 5 mL) was added sodium nitrite (0.5 g, 7.2 mmol) over 3 min at 0° C. The mixture was stirred at 0° C. for 30 min before a solution of tin(II) chloride (2.7 g, 14.4 mmol in 5 mL concentrated hydrochloric acid) was added at 0° C. over 5 min. After stirring at 0° C. for 10 min and rt for 1 hr, the reaction mixture was filtered. The solid was washed with water (10 mL), 4N aqueous sodium hydroxide solution, and water (10 mL). The solid was dissolved in dichloromethane (20 mL), washed with brine (10 mL), dried (Na2SO4), and concentrated. Silica gel flash chromatography gave 6-bromo-3-phenyl-1H-indazole (0.42 g, 1.5 mmol, 42% yield).

後処理

  1. additionwas added at 0° C. over 5 min
  2. filtrationthe reaction mixture was filtered
  3. washThe solid was washed with water (10 mL), 4N aqueous sodium hydroxide solution, and water (10 mL)
  4. dissolutionThe solid was dissolved in dichloromethane (20 mL)
  5. washwashed with brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-aed51e37008c421ea37b24f2b8e5d42d
出典データセット
uspto-grants-2011_11
特許番号
US08067447B2

反応ノート

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