N-bromobutanimide → 3-Bromo-6-methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine

HRID 539738

反応式

HRID 539738 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=3)[N:11]=2)[N:8]=1.[Br:22]N1C(=O)CCC1=O>C(#N)C.O.C([O-])(O)=O.[Na+]>[Br:22][C:9]1[N:7]2[N:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]2=[N:11][C:10]=1[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1

参加物

6

反応物 2

HCID 67184N-bromobutanimideHCID 680891556-Methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine

生成物 1

HCID 680890483-Bromo-6-methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine収率 94%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of 6-methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine (0.250 g, 0.879 mmol) in acetonitrile (20 mL) is added N-bromosuccinimide (0.879 mmol) and the mixture is heated at 60° C. for 8 hours. The reaction mixture is diluted with water (50 mL) and sat. aqueous NaHCO3 (50 mL). The precipitate that forms is collected by filtration, washed with water (3×25 mL) and dried under vacuum to give the title product (0.300 g, 94% yield) as a yellow solid: Rf 0.51 (1:1 EtOAc:hexanes); LCMS (m/z)=363.2, 365.2 [M+H]+, tR=3.02 min.

後処理

  1. filtrationThe precipitate that forms is collected by filtration
  2. washwashed with water (3×25 mL)
  3. customdried under vacuum

出典と根拠

ORDレコード
ord-344448864cad43119ae634d045403660
出典データセット
uspto-grants-2014_10
特許番号
US08871767B2

関連ノート

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