N-bromobutanimide → 7-Bromo-3,6,6-trimethyl-1-pyridin-2-yl-5,7-dihydroindazol-4-one

HRID 2084282

Reaction equation

HRID 2084282 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:15]2[CH2:14][C:13]([CH3:17])([CH3:16])[CH2:12][C:11](=[O:18])[C:10]=2[C:9]([CH3:19])=[N:8]1.[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:20][CH:14]1[C:15]2[N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[N:8]=[C:9]([CH3:19])[C:10]=2[C:11](=[O:18])[CH2:12][C:13]1([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 41652463,6,6-Trimethyl-1-pyridin-2-yl-5,7-dihydroindazol-4-one

Product 1

HCID 40739867-Bromo-3,6,6-trimethyl-1-pyridin-2-yl-5,7-dihydroindazol-4-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(2-pyridyl)-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazole (0.25 g, 0.98 mmol), prepared as described in example 3, and N-bromosuccinimide (0.180 g, 0.98 mmol) in chloroform (6 ml) was stirred at 60° C. for about 4 hours and then washed with water. The organic phase was dried over sodium sulfate and evaporated to dryness. The residue was chromatographed on silica gel (cyclohexane:ethyl acetate=90:10). The title compound was obtained as a colourless solid (0.28 g, 85%): m.p 160-161° C.

Workup

  1. customprepared
  2. washwashed with water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel (cyclohexane:ethyl acetate=90:10)

Sources & evidence

ORD record
ord-445e38361a5948df8fe163982b494a9a
Source dataset
uspto-grants-2004_04
Patent number
US06716856B1

Linked notes

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