Iodoethane → 5-ethyl-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one

HRID 341062Notes

Reaction equation

HRID 341062 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20](=[O:21])[C:11]2=[CH:12][NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]2=[N:9]1.I[CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH2:23]([N:13]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[C:10]2=[N:9][N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[C:20](=[O:21])[C:11]2=[CH:12]1)[CH3:24]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178515185HCID 178515185, compound

Product 1

HCID 529146085-ethyl-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(2-Fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (51 mg, 0.18 mmol) was dissolved in dimethylsulfoxide (1 mL) and treated with iodoethane (0.018 mL, 0.22 mmol, 1.2 equiv) and potassium carbonate (30 mg, 0.22 mmol, 1.2 equiv). The mixture was stirred at ambient temperature for 14 hours, filtered and purified by preparative reverse phase HPLC (82:20 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 8.78 (1H, s), 8.48 (1H, dd, J=8.0, 1.5 Hz), 7.74-7.58 (4H, m), 7.42-7.36 (1H, m), 7.29-7.23 (2H, m), 4.44 (1H, q, J=7.4 Hz), 1.64 (3H, t, J=7.2 Hz) ppm; low resolution mass spectrometry (ES+) m/z 308.0 [(M+H)+; calculated for C18H15FN3O: 308.1].

Workup

  1. filtrationfiltered
  2. custompurified by preparative reverse phase HPLC (82:20 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-2a96b201e0e14b749b8715df3f9c83f2
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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