Pyridine → HCID 59179416, compound

HRID 2389890Notes

Reaction equation

HRID 2389890 reaction equation
[O:1]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([CH2:10][CH2:11][C:12]([NH2:14])=O)[C:4]=2[CH2:3][CH2:2]1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl.C(=O)([O-])O.[Na+]>[O:1]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([CH2:10][CH2:11][C:12]#[N:14])[C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 59179438HCID 59179438, compound

Product 1

HCID 59179416HCID 59179416, compoundYield 33.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-(2,3-dihydrofuro[3,2-c]pyridin-4-yl)propanamide (435 mg, 2.26 mmol) in dichloromethane (10 mL) were added pyridine (384 μL, 4.75 mmol) and trifluoroacetic anhydride (384 μL, 2.72 mmol), and the mixture was stirred at room temperature for 13 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=30/70→70/30) to give the title compound (132 mg, yield 33%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=30/70→70/30)

Sources & evidence

ORD record
ord-1f1558463ae845fc9cd64aa8d065957e
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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