Sodium Hydroxide → 5-Bromo-4-fluoro-1H-indazole

HRID 1057112ノート

反応式

HRID 1057112 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[C:3]=1[F:10].[N:11]([O-])=O.[Na+].[OH-].[Na+]>CC(O)=O>[Br:1][C:2]1[C:3]([F:10])=[C:4]2[C:5](=[CH:7][CH:8]=1)[NH:6][N:11]=[CH:9]2

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 157466844-Bromo-3-fluoro-2-methylanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 454803935-Bromo-4-fluoro-1H-indazole収率 75.9%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 4-bromo-3-fluoro-2-methylaniline (20 g, 98.0 mmol) in CH3CO2H (600 mL) was added NaNO2 (8.1 g, 118 mmol) at 10° C. The resulting mixture was stirred at room temperature for 4 hours. Upon completion, aqueous NaOH (50%) was added to the reaction mixture until pH was ˜7-8. The mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (0˜40% EtOAc in petroleum ether) affording the title compound (16 g). 1H NMR (300 MHz, DMSO-d6): δ 13.58 (br, 1H), 8.22 (s, 1H), 7.53 (t, 1H), 7.38 (d, 1H).

後処理

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (0˜40% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-d9a6cc72acc04742b005bd673c273d5a
出典データセット
uspto-grants-2016_07
特許番号
US09399646B2

反応ノート

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