2-Aminopyridine → HCID 60202592, compound

HRID 526067Notes

Reaction equation

HRID 526067 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)[CH:6]=[C:5]2[C:17]([NH:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)=[O:18].[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[O:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[C:7]1[CH:6]=[C:5]([C:17]([NH:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[O:18])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[CH:3]=2)[N:8]=1

Participants

5

Reactant 2

HCID 104392-AminopyridineHCID 46238383HCID 46238383, compound

Product 1

HCID 60202592HCID 60202592, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

6-bromo-2-(furan-2-yl)-N-(pyridin-3-yl)quinoline-4-carboxamide (prepared as described above, 0.080 g) was added to a sealed tube and dissolved in toluene (5 ml). The vessel was purged with argon for 5 minutes, and 2-aminopyridine (0.029 g, 1.50 eq.) was then added. The vessel was purged with argon for an additional 5 minutes, cesium carbonate (0.200 g) was added, and the tube was purged with argon for an additional 15 minutes. DavePhos (2-(2-dicyclohexylphosphanylphenyl)-N,N-dimethylaniline, 0.012 g) and Pd2(dba)3 (tris(dibenzylideneacetone)dipalladium(0), 0.014 g) were added, the tube was flushed with argon and sealed. The reaction mixture was heated to 90° C. for 16 hours, and 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), filtered through celite bed, which was washed with ethyl acetate (3*10 ml). The ethyl acetate was removed by distillation and the crude product was subjected to silica gel column chromatography purification. Elution of the compound with 20% ethyl acetate in hexanes provided 2-(furan-2-yl)-6-(pyridin-2-ylamino)-N-(pyridin-3-yl)quinoline-4-carboxamide (0.015 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.06 (s, 1H), 9.62 (s, 1H), 8.99 (m, 1H), 8.57 (m, 1H), 8.41 (m, 1H), 8.27 (m, 2H), 8.05 (m, 2H), 8.00 (m, 1H), 7.95 (m, 1H), 7.61 (m, 1H), 7.50 (m, 1H), 7.38 (m, 1H), 6.92 (m, 1H), 6.81 (m, 1H), 6.74 (m, 1H); m/z 408.2 (MH+).

Workup

  1. customThe vessel was purged with argon for 5 minutes
  2. customThe vessel was purged with argon for an additional 5 minutes
  3. additioncesium carbonate (0.200 g) was added
  4. customthe tube was purged with argon for an additional 15 minutes
  5. additionDavePhos (2-(2-dicyclohexylphosphanylphenyl)-N,N-dimethylaniline, 0.012 g) and Pd2(dba)3 (tris(dibenzylideneacetone)dipalladium(0), 0.014 g) were added
  6. customthe tube was flushed with argon
  7. customsealed
  8. customAfter completion of the reaction
  9. filtrationfiltered through celite bed, which
  10. washwas washed with ethyl acetate (3*10 ml)
  11. customThe ethyl acetate was removed by distillation
  12. customthe crude product was subjected to silica gel column chromatography purification
  13. washElution of the compound with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3cd459131db6458c900c0eda97b2a318
Source dataset
uspto-grants-2016_05
Patent number
US09345700B2

Reaction notes

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