2,4-Difluoronitrobenzene → HCID 66589191, compound

HRID 1092234Notes

Reaction equation

HRID 1092234 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CCN(C(C)C)C(C)C.[CH:21]1([C:24]2[NH:28][N:27]=[C:26]([NH2:29])[CH:25]=2)[CH2:23][CH2:22]1>C1COCC1>[CH:21]1([C:24]2[NH:28][N:27]=[C:26]([NH:29][C:2]3[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=3[N+:9]([O-:11])=[O:10])[CH:25]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

Product 1

HCID 66589191HCID 66589191, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 2,4-difluoro-1-nitrobenzene (1.76 g, 11.1 mmol) and DIEA (1.93 ml, 11.1 mmol) in THF (20 ml) was added dropwise a solution of 5-cyclopropyl-1H-pyrazol-3-amine (0.91 g, 7.39 mmol) in THF (5 ml) at 25° C. After addition, the reaction mixture was stirred at 80° C. for 48 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane:DCM:EtOAc=2:1:1) to give the title compound as a yellow solid (0.62 g, 32%). NMR (400 MHz) 12.37 (s, 1H), 9.83 (s, 1H), 8.25 (m, 1H), 7.98 (d, J=11.2 Hz, 1H), 6.75 (m, 1H), 5.95 (s, 1H), 1.90 (m, 1H), 0.96 (m, 2H), 0.72 (m, 2H).

Workup

  1. additionAfter addition
  2. customThe solvent was removed under reduced pressure
  3. customthe resulted residue was purified by column chromatography (hexane:DCM:EtOAc=2:1:1)

Sources & evidence

ORD record
ord-e53f6bc1ccf243dd8f69ec93afa87ed0
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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