4-Acetylpyridine → HCID 53758566, compound

HRID 659941Notes

Reaction equation

HRID 659941 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].[C:7]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)(=O)[CH3:8].[NH2:16][C:17]1[C:18](Cl)=[N:19][CH:20]=[CH:21][CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(O)(=O)C.CC(N(C)C)=O>[N:13]1[CH:14]=[CH:15][C:10]([C:7]2[NH:16][C:17]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:8]=2)=[CH:11][CH:12]=1

Participants

9

Reactant 5

HCID 142824-AcetylpyridineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 53758566HCID 53758566, compoundYield 58.9%

Reagents, catalysts & solvents 3

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 176Acetic AcidSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

Into 12 mL dimethylacetamide are added 240 mg (2 mmoles) of anhydrous magnesium sulfate, 1.3 mL (12 mmoles) of 4-acetyl pyridine, 515 mg (4 mmoles) of 3-amino-2-chloropyridine and 0.3 mL of acetic acid. The resulting suspension is kept under argon. Then 1.1 g (5.2 mmoles) of potassium phosphate and 202 mg (0.4 mmole) of bis-(tri-t-butylphosphine) palladium are added to the reaction mixture which is then sealed in its reaction vessel and stirred at 140° C. for 10 hours. The reaction mixture is poured into ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. The solid residue after concentration is purified by chromatography on silica gel (ethylacetate/methanol 9/1) to give 460 mg 2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine as brown solid.

Workup

  1. customis then sealed in its reaction vessel
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solid residue after concentration
  6. customis purified by chromatography on silica gel (ethylacetate/methanol 9/1)

Sources & evidence

ORD record
ord-ad5b7674ebdf403c9f8b1e6b6a2706b0
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

Loading…