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

HRID 563391노트

반응식

HRID 563391 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 573551936-Bromo-3-phenyl-1H-indazole수율 42%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-aed51e37008c421ea37b24f2b8e5d42d
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067447B2

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