Bromine → HCID 46197587, compound

HRID 2261249Notes

Reaction equation

HRID 2261249 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14]2[N:15]([CH3:20])[C:16](=[O:19])[CH:17]=[CH:18][C:13]=2[CH:12]=[N:11]1>C(O)(=O)C.O>[Br:1][C:17]1[C:16](=[O:19])[N:15]([CH3:20])[C:14]2[N:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[Cl:3])[N:11]=[CH:12][C:13]=2[CH:18]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 68737843HCID 68737843, compound

Product 1

HCID 46197587HCID 46197587, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

At RT, bromine (206 mg, 1.29 mmol) was added to a solution of 1(2-chlorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (319 mg, 1.23 mmol) in 1.5 mL of glacial acetic acid. After stirring at RT for 30 min, it was diluted with water and stirred for 5 min. The precipitated white solid was filtered off and rinsed with water, collected and dried to afford 5-bromo-1-(2-chlorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (323 mg). The filtrate was extracted three times with EtOAc. The combined EtOAc layers were washed with 2 N NaOH followed by brine, dried and concentrated to afford additional 5-bromo-1-(2-chlorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (82 mg). The crude material was used without further purification. MS (ESI, pos.ion) m/z: 338.0/340.0 (M+1).

Workup

  1. stirringstirred for 5 min
  2. filtrationThe precipitated white solid was filtered off
  3. washrinsed with water
  4. customcollected
  5. customdried

Sources & evidence

ORD record
ord-05e88e68a78249cea3e91ba1e00086fd
Source dataset
uspto-grants-2010_12
Patent number
US07846944B2

Reaction notes

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