N-bromobutanimide → 4-(3-Bromo-1H-indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one

HRID 2234081Notes

Reaction equation

HRID 2234081 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[C:11](=[O:22])[NH:12][N:13]=[C:14]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:15]=1.[Br:23]N1C(=O)CCC1=O>CC(C)=O>[Br:23][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]=1[C:10]1[C:11](=[O:22])[NH:12][N:13]=[C:14]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1356875534-(1H-Indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one

Product 1

HCID 1355255444-(3-Bromo-1H-indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

22 mg 4-(1H-Indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one is suspended in 30 mL acetone and 2 mg N-bromosuccinimide is added. The reaction mixture is stirred for 3 hours at room temperature, the precipitated product isolated by filtration and washed with aceton. The product is purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (0.05% HCOOH). Yield 11.2 mg. LC-MS (ES+) 368 (M+H)+.

Workup

  1. customthe precipitated product isolated by filtration
  2. washwashed with aceton
  3. customThe product is purified by preparative RP-HPLC
  4. washeluting with a gradient of 0-100% acetonitrile in water (0.05% HCOOH)

Sources & evidence

ORD record
ord-fa5e673ff2fc4baaa626a8d23e135bf0
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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