Water → HCID 60202493, compound

HRID 526073Notes

Reaction equation

HRID 526073 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]([NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[CH3:34][C:35]1[O:39][C:38](B(O)O)=[CH:37][CH:36]=1>O1CCOCC1.C(OCC)(=O)C>[CH3:34][C:35]1[O:39][C:38]([C:2]2[CH:11]=[C:10]([C:12]([NH:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[O:13])[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:8]=3)[N:3]=2)=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343725-Methyl-2-furanboronic AcidHCID 88923534HCID 88923534, compound

Product 1

HCID 60202493HCID 60202493, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a round-bottomed flask under argon atmosphere was added 2-chloro-6-phenyl-N-(pyridin-3-yl)quinoline-4-carboxamide (0.100 g) in 1,4-dioxane (3 ml), and the vessel was purged with argon under stirring for 5 minutes. After 5 minutes, a 2N solution of potassium carbonate in water (11 eq) was added and the flask was purged with argon under stirring for 5 minutes. (5-methylfuran-2-yl)boronic acid (1.5 eq) was then added and the tube was purged with argon under stirring for 15 minutes. Finally, palladium(0)tetrakis triphenylphosphine (0.05 eq) was added under argon and the flask was affixed to a reflux condenser and heated to 90° C. for 5 hours. The completion of the reaction was monitored on TLC using ethyl acetate:hexanes as a mobile phase. After completion of the reaction, reaction mixture was diluted with ethyl acetate (100 ml) and then washed with water (5*100 ml). The ethyl acetate layer was dried over anhydrous sodium sulphate and then solvent was distilled out and the crude was subjected to purification by silica gel column chromatography to provide 0.01 g of 2-(5-methylfuran-2-yl)-6-phenyl-N-(pyridin-3-yl)quinoline-4-carboxamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.12 (s, 1H), 8.97 (s, 1H), 8.41 (m, 1H), 8.39 (s, 1H), 8.30 (m, 1H), 8.19 (m, 3H), 7.78 (m, 2H), 7.55 (m, 2H), 7.48 (m, 1H), 7.44 (m, 2H), 6.43 (broad s, 1H), 2.48 (s, 3H); m/z 406.2 (MH+).

Workup

  1. customthe vessel was purged with argon
  2. waitAfter 5 minutes
  3. customthe flask was purged with argon
  4. stirringunder stirring for 5 minutes
  5. customthe tube was purged with argon
  6. stirringunder stirring for 15 minutes
  7. customthe flask was affixed to a reflux condenser
  8. customAfter completion of the reaction, reaction mixture
  9. washwashed with water (5*100 ml)
  10. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulphate
  11. distillationsolvent was distilled out
  12. customthe crude was subjected to purification by silica gel column chromatography

Sources & evidence

ORD record
ord-8b7cf705fc1b4c8c92c55d34d1b0ca77
Source dataset
uspto-grants-2016_05
Patent number
US09345700B2

Reaction notes

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