Cyanuric chloride → 6-Bromo-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carbonitrile

HRID 1048894Notes

Reaction equation

HRID 1048894 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH:7]=[C:6]([C:19]([NH2:21])=O)[C:5]2=[O:22].N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[CH:7]=[C:6]([C:19]#[N:21])[C:5]2=[O:22]

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 1214478716-Bromo-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

Product 1

HCID 1214479376-Bromo-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carbonitrileYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound E (30 mg, 0.083 mmol, 1.0 eq) and cyanuric chloride (15 mg, 0.083 mmol, 1.0 eq) were dissolved in DMF (0.5 mL) and the reaction was stirred at room temperature for 30 minutes. The reaction was diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. Purification by reverse phase chromatography afforded 10.1 mg (68%) of the title compound as white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.94 (s, 1H), 8.30 (d, J=2.4 Hz, 1H), 7.86 (dd, J=9.0, 2.4 Hz, 1H), 7.75-7.72 (m, 2H), 7.53 (t, J=8.7 Hz, 2H), 6.96 (d, J=9.1 Hz, 1H); ES-MS [M+1]+: 343.2.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by reverse phase chromatography

Sources & evidence

ORD record
ord-5b7531a8fa6d450f9b420c96739bdbc5
Source dataset
uspto-grants-2016_07
Patent number
US09382208B1

Reaction notes

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