5-Bromoindole → HCID 60202491, compound

HRID 526069Notes

Reaction equation

HRID 526069 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:15]=[C:14]([C:16](=[O:24])[NH:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11](B(O)O)[CH:12]=2)[N:7]=1.Br[C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][CH:33]=[CH:32]2>CN(C=O)C.C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:15]=[C:14]([C:16]([NH:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[O:24])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:29]3[CH:30]=[C:31]4[C:35](=[CH:36][CH:37]=3)[NH:34][CH:33]=[CH:32]4)[CH:12]=2)[N:7]=1

Participants

5

Reactant 2

HCID 249055-BromoindoleHCID 68288695HCID 68288695, compound

Product 1

HCID 60202491HCID 60202491, compoundYield 6.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a sealed tube under argon atmosphere was added (2-(furan-2-yl)-4-(pyridin-3-ylcarbamoyl)quinolin-6-yl)boronic acid (0.120 g) in DMF (4 ml) and the vessel was purged with argon under stirring for 5 minutes. After 5 minutes, a 2N aqueous solution of potassium carbonate was added (1.8 ml, 11 eq) and the tube was purged with argon under stirring for 5 minutes. 5-bromoindole (0.057 g, 0.9 eq) was then added and the vessel was purged with argon under stirring for 15 minutes. Finally tetrakistriphenylphosphine palladium(0) (0.011 g, 0.03 eq.) was added under argon and the tube was sealed. The reaction mixture was heated to 90° C. for 5 hours. The completion of the reaction was monitored by TLC using ethyl acetate:hexanes (5:5) as a mobile phase. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (10 ml) and then washed with water (5*10 ml). The ethyl acetate layer was dried over anhydrous sodium sulfate and the solvent was removed by distillation and the crude product was subjected to purification by high performance liquid chromatography to provide 2-(furan-2-yl)-6-(1H-indol-5-yl)-N-(pyridin-3-yl)quinoline-4-carboxamide (0.008 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.34 (s, 1H), 11.19 (s, 1H), 9.00 (m, 1H), 8.41 (m, 1H), 8.35 (m, 1H), 8.30 (m, 1H), 8.20 (m, 1H), 8.12 (m, 2H), 7.85 (m, 1H), 7.70 (m, 1H), 7.4 (m, 1H), 7.58 (m, 1H), 7.50 (m, 2H), 7.43 (m, 1H), 7.12 (m, 1H), 6.54 (m, 1H); m/z 431.2 (MH+).

Workup

  1. customthe vessel was purged with argon
  2. waitAfter 5 minutes
  3. additiona 2N aqueous solution of potassium carbonate was added (1.8 ml, 11 eq)
  4. customthe tube was purged with argon
  5. stirringunder stirring for 5 minutes
  6. customthe vessel was purged with argon
  7. stirringunder stirring for 15 minutes
  8. customthe tube was sealed
  9. customAfter completion of the reaction
  10. washwashed with water (5*10 ml)
  11. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  12. customthe solvent was removed by distillation
  13. customthe crude product was subjected to purification by high performance liquid chromatography

Sources & evidence

ORD record
ord-3bc33ecdeca645d6999f14579ea6c9f2
Source dataset
uspto-grants-2016_05
Patent number
US09345700B2

Reaction notes

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