Bromine → 2-Methylpentane

HRID 1357471Notes

Reaction equation

HRID 1357471 reaction equation
[C:1]1([C:7]2[N:8]=[N:9][CH:10]=[C:11]3[CH:16]=[CH:15][C:14](=[O:17])[NH:13][C:12]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:18]Br>C(O)(=O)C>[CH3:4][CH2:3][CH2:2][CH:1]([CH3:7])[CH3:6].[Br:18][C:15]1[C:14](=[O:17])[NH:13][C:12]2=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[N:9][CH:10]=[C:11]2[CH:16]=1

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 11593771HCID 11593771, compound

Product 2

HCID 78922-MethylpentaneHCID 18186435HCID 18186435, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8-Phenyl-1H-pyrido[2,3-d]pyridazin-2-one (46 mg) and bromine (0.11 ml) were stirred together in acetic acid (3 ml) at 90° C. for 7 days, adding a fresh aliquot of bromine (0.11 ml) every 24 h. The mixture was allowed to cool to room temperature, precipitating a solid. This was separated by filtration and purified by flash chromatography on silica gel, eluting with 1:1 ethyl acetate:isohexane, then 100% ethyl acetate, yielding 3-bromo-8-phenyl-1H-pyrido[2,3-d]pyridazin-2-one as a pale yellow solid (10 mg). 1H NMR (400 MHz, CDCl3) δ7.67 (5H, m), 8.29 (1H, s), 9.02 (1H, br s), 9.21 (1H, s); MS (ES+) m/e 302, 304 [MH]+.

Workup

  1. customprecipitating a solid
  2. customThis was separated by filtration
  3. custompurified by flash chromatography on silica gel
  4. washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-1e3b8b9fdcdf478ab4496eeb981e9583
Source dataset
uspto-grants-2003_07
Patent number
US06593325B1

Reaction notes

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