4-Aminopyridine → HCID 11371013, compound

HRID 2249871Notes

Reaction equation

HRID 2249871 reaction equation
[F:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[N:4][C:5]2[C:10]([C:11]=1I)=[CH:9][CH:8]=[CH:7][CH:6]=2.CC(C)([O-])C.[Na+].[NH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.O>[F:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[N:4][C:5]2[C:10]([C:11]=1[NH:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 17274-AminopyridineHCID 11566815HCID 11566815, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 11371013HCID 11371013, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-fluoro-2-(2-fluoro-phenyl)-4-iodo-quinoline (from Step F, 0.02 g, 0.05 mmol) in toluene (1 mL) was added S-BINAP (0.007 g, 0.01 mmol), sodium tert-butoxide (0.105 g, 1 mmol) and 4-aminopyridine (0.015 g, 0.05 mmol). The resulting mixture was degassed for 5 min., after which tris(dibenzylidineacetone) dipalladium(0) (0.0025 g, 0.0025 mmol) was added. The reaction mixture was heated to 110° C. for 48 h. and then diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in rotary evaporator. The residue was purified using HPLC over a gradient of acetonitrile and water containing 0.1% trifluoroacetic acid to yield the desired compound (0.012 g, 65%). MS (ES) 334.1 (M+H)+.

Workup

  1. customThe resulting mixture was degassed for 5 min.
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in rotary evaporator
  5. customThe residue was purified

Sources & evidence

ORD record
ord-455baf2234f44cd482150d2fb9399c9b
Source dataset
uspto-grants-2008_01
Patent number
US07314939B2

Reaction notes

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