N-bromobutanimide → 3-Bromo-5-cyclopropyl-2-(5-methylpyridin-2-yl)-6-nitro-2H-indazole

HRID 63533ノート

反応式

HRID 63533 の反応式
[CH:1]1([C:4]2[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]3[C:6](=[CH:7][N:8]([C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1.[Br:23]N1C(=O)CCC1=O>CN(C=O)C>[Br:23][C:7]1[N:8]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=2)[N:9]=[C:10]2[C:6]=1[CH:5]=[C:4]([CH:1]1[CH2:3][CH2:2]1)[C:12]([N+:13]([O-:15])=[O:14])=[CH:11]2

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 866989485-Cyclopropyl-2-(5-methylpyridin-2-yl)-6-nitro-2H-indazole

生成物 1

HCID 866989493-Bromo-5-cyclopropyl-2-(5-methylpyridin-2-yl)-6-nitro-2H-indazole収率 100%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of (ii) (1.08 g, 3.67 mmol) in DMF (15 mL) was added N-bromosuccinimide (780 mg, 4.40 mmol) and the resulting mixture stirred at 80° C. for 1.5 h. The reaction mixture was then cooled to RT and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed with aq. saturated sodium bicarbonate (20 mL) and brine (20 mL). The organic phase was dried (MgSO4) and the volatiles removed in vacuo to give (iii) (1.37 g, >99%). ESI-MS: calculated [M+H]+ 373.01375.0. observed [M+H]+ 373.1/375.1.

後処理

  1. temperatureThe reaction mixture was then cooled to RT
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (100 mL)
  4. washwashed with aq. saturated sodium bicarbonate (20 mL) and brine (20 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe volatiles removed in vacuo

出典と根拠

ORDレコード
ord-e65bb998b6db4aa2915061dc575f6af6
出典データセット
uspto-grants-2016_09
特許番号
US09447080B2

反応ノート

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