Dichloromethane → HCID 69935613, compound

HRID 341106Notes

Reaction equation

HRID 341106 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]3=[N:19][NH:20][C:21](=[O:22])[C:11]3=[CH:10]2)=[N:6][CH:7]=1.[H-].[Na+].[CH2:25](Br)[CH:26]=[CH2:27].ClCCl>CS(C)=O>[CH2:27]([N:20]1[C:21](=[O:22])[C:11]2=[CH:10][N:9]([CH2:8][C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=3)[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]2=[N:19]1)[CH:26]=[CH2:25]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 69935349HCID 69935349, compound

Product 1

HCID 69935613HCID 69935613, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-[(5-Bromopyridin-2-yl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (250 mg, 0.704 mmol) was dissolved in dimethylsulfoxide (3 mL) and treated with sodium hydride (70.4 mg, 1.76 mmol, 2.5 equiv) and allyl bromide (170 mg, 1.41 mmol, 2.0 equiv). The mixture was stirred at ambient temperature for 18 hours, poured into dichloromethane (50 mL) and washed with sodium bicarbonate (2×50 mL, aqueous saturated) and brine (1×50 mL). The organic extract was dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (eluting 80:20 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid), providing the title compound: 1H-NMR (400 MHz, CD3OD) δ 8.90 (1H, s), 8.56 (1H, s), 8.34 (1H, d, J=9.0 Hz), 7.99 (1H, d, J=6.2 Hz), 7.74 (1H, d, J=8.2 Hz), 7.63-7.55 (2H, m), 7.42 (1H, d, J=8.4 Hz), 6.07-5.98 (1H, m), 5.81 (2H, s), 5.24-5.16 (2H, m), 4.86 (2H, s), ppm; low resolution mass spectrometry (ES+) m/z 396.8 (81Br) [(M+H)+; calculated for C19H15BrN4O: 397.0].

Workup

  1. washwashed with sodium bicarbonate (2×50 mL, aqueous saturated) and brine (1×50 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative reverse phase HPLC (eluting 80:20 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-4b44b42572ab4e518472dae31956cdce
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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