2-Aminopyridine → 2-Pyridyl-2-quinolylamine

HRID 523894Notes

Reaction equation

HRID 523894 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(O[K])(C)(C)C>C1(C)C=CC=CC=1.C(Cl)Cl.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]>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:12][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 3

HCID 104392-AminopyridineHCID 27627562-BromoquinolineHCID 178418922HCID 178418922, compound

Product 1

HCID 53401122-Pyridyl-2-quinolylamineYield 45%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

2-Bromoquinoline, I (500 mg, 2.40 mmol), 2-aminopyridine (249 mg, 2.64 mmol), tBuOK (404 mg, 3.60 mmol), (±)-BINAP (6 mg, 0.01 mmol) and Pd2(dba)3 (5.5 mg, 0.006 mmol) were stirred in toluene (10 mL) at 90° C. under Ar(g) for 21 h. The reaction mixture was then diluted with CH2Cl2 (10 mL) and silica was added, followed by the removal of the solvent under reduced pressure. The resulting dry load material was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:1 then 100:2) to furnish II as a colourless oil (344 mg, 45%).

Workup

  1. additionwas added
  2. customfollowed by the removal of the solvent under reduced pressure
  3. customThe resulting dry load material
  4. customwas purified by silica gel column chromatography
  5. washeluting with CH2Cl2/MeOH (100:1

Sources & evidence

ORD record
ord-e549f2b912d741d4855b89aa96f59625
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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