2-Aminopyridine → HCID 90387822, compound

HRID 874465Notes

Reaction equation

HRID 874465 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[C:19]2[C:14](=[C:15]([O:20][CH3:21])[N:16]=[CH:17][CH:18]=2)[N:13]([CH3:22])[CH:12]=1.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.CC([O-])(C)C.[K+]>CS(C)=O>[CH3:21][O:20][C:15]1[N:16]=[CH:17][CH:18]=[C:19]2[C:11]([C:3]3[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=3[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:12][N:13]([CH3:22])[C:14]=12

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 23665647Potassium tert-butoxideHCID 90387914HCID 90387914, compound

Product 1

HCID 90387822HCID 90387822, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of Example 23a (0.122 g, 0.405 mmol) and 2-aminopyridine (0.042 g, 0.445 mmol) in dimethyl sulfoxide (6 mL) was treated with potassium 2-methylpropan-2-olate (0.091 g, 0.81 mmol) and stirred at ambient temperature for 23.5 hours. The reaction mixture was partitioned between ethyl acetate and water, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 0-15% ethyl acetate in dichloromethane) to give 0.117 g (77%) of the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica gel, 0-15% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-02a0c128f6134ac1bb0980bff4c6210b
Source dataset
uspto-grants-2015_03
Patent number
US08980879B2

Reaction notes

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