1,1'-Carbonyldiimidazole → HCID 136336852, compound

HRID 69101Notes

Reaction equation

HRID 69101 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[N:13]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[N:12]=[CH:11][CH:10]=2)=[C:6]([CH:8]=1)[NH2:7].C1N=CN([C:24](N2C=NC=C2)=[O:25])C=1>CN1CCCC1=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[N:13]([CH:14]4[CH2:18][CH2:17][CH2:16][CH2:15]4)[N:12]=[CH:11][C:10]=3[C:24](=[O:25])[NH:7][C:6]=2[CH:8]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86694305HCID 86694305, compound

Product 1

HCID 136336852HCID 136336852, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 100 mg of 5-bromo-2-(1-cyclopentyl-1H-pyrazol-5-yl)aniline in 2.5 mL of N-methylpyrrolidone was added 105 mg of CDI, followed by stirring at 150° C. for 2 hours using a microwave reactor, and cooling to room temperature. The precipitated solid was collected by filtration, washed with ethyl acetate, and then dried under reduced pressure to obtain 73 mg of 7-bromo-1-cyclopentyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one.

Workup

  1. temperaturecooling to room temperature
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with ethyl acetate
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-0b36c0b483a14ecfa4c09dbabfc7694b
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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