Bromine → HCID 66661444, compound

HRID 1047643Notes

Reaction equation

HRID 1047643 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[Br:21]Br>C(#N)C>[Br:21][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:12]=2)[N:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[N:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 66661508HCID 66661508, compound

Product 1

HCID 66661444HCID 66661444, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 1-(4-methylphenyl)-1H-indazole-5-carboxylate (327.1 mg, 1.228 mmol) was dissolved in acetonitrile (12.300 mL) at 25° C. Bromine (158 μL, 3.0575 mmol) was added dropwise and the reaction mixture was allowed to stir for 30 min. The reaction was stopped, quenched by addition of saturated aqueous sodium hydrogen carbonate (20 mL), and extracted with ethyl acetate (3×20 mL). The combined organic phases were washed with saturated aqueous sodium chloride (1×20 mL), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure. The crude product was purified by flash chromatography (RediSep SiO2, 40 g column) on a CombiFlash Rf purification system eluting with ethyl acetate-hexanes (0-45%). The title compound (407.3 mg, 1.180 mmol, 96% yield) was recovered as a light yellow/white solid. LC-MS: [M+1]=346.1.

Workup

  1. customquenched by addition of saturated aqueous sodium hydrogen carbonate (20 mL)
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic phases were washed with saturated aqueous sodium chloride (1×20 mL)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified by flash chromatography (RediSep SiO2, 40 g column) on a CombiFlash Rf purification system
  8. washeluting with ethyl acetate-hexanes (0-45%)

Sources & evidence

ORD record
ord-376d640e44a146838bc36c90a69cb7cb
Source dataset
uspto-grants-2013_10
Patent number
US08569512B2

Reaction notes

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