2-Chloropyridine → HCID 59813700, compound

HRID 1925349Notes

Reaction equation

HRID 1925349 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([NH2:26])=[CH:21][CH:20]=[CH:19]2.Cl[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.CC([O-])(C)C.[Na+].C([O-])(O)=O.[Na+]>O1CCOCC1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([NH:26][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)=[CH:21][CH:20]=[CH:19]2

Participants

8

Reactant 4

HCID 79772-ChloropyridineHCID 516892Sodium BicarbonateHCID 23676156Sodium t-butoxideHCID 675202746-(6,7-Dimethoxyquinolin-4-yloxy)naphthalen-1-amine

Product 1

HCID 59813700HCID 59813700, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-(6,7-dimethoxyquinolin-4-yloxy)naphthalene-1-amine (150 mg, 0.43 mmol), 2-chloropyridine (45 μl, 0.47 mmol), and NaOtBu (52.0 g, 160 mmol) in dioxane (4 mL) were added Pd2(dba)3 (12 mg, 0.01 mmol) and 2-(dicyclohexylphosphino)-2′-4′-6′-tri-i-propyl-1,1′-biphenyl (25 mg, 0.05 mmol). The resulting mixture was heated at 100° C. for 3 h. After cooling to ambient temperature, the mixture was diluted with EtOAc (25 mL) and poured into sat'd NaHCO3 (50 mL). The phases were separated and the aqueous phase was extracted with EtOAc (2×25 mL). The organic layers were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo. The derived residue was purified by silica gel chromatography (0-10% CH3OH in CH2Cl2) to provide the title compound as a white solid. MS (ESI, pos. ion) m/z: 424.1 (M+1). Mass Calc'd for C26H21N3O3: 423.46.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc (2×25 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe derived residue was purified by silica gel chromatography (0-10% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-351db496b42c4e3499b0ed9f163149a1
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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