Pyridine → HCID 19022613, compound

HRID 1034450Notes

Reaction equation

HRID 1034450 reaction equation
COC([CH:5]1[CH:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:10][C:9]2[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=2[NH:7][C:6]1=[O:24])=O.N1C=CC=CC=1.[I-].[Li+]>C(OCC)(=O)C>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]2[CH2:10][C:9]3[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=3[NH:7][C:6](=[O:24])[CH2:5]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 66321Lithium iodideHCID 14156196HCID 14156196, compound

Product 1

HCID 19022613HCID 19022613, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.0 g (3.08 mmol) of 2,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-1H-1-benzazepin-2-one [prepared by the method of Floyd, et al., J. Med. Chem., 35, 756-772 (1992)]in 10 mL of pyridine was treated with 1.65g (12.3 mmol, 4eq) of lithium iodide and the resulting mixture refluxed in an oil bath under a nitrogen atmosphere for 20 hours. The dark brown mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with 1N HCl (3×50 mL) and water, dried over anhydrous magnesium sulfate and filtered. Evaporation of the solvent followed by column chromatography on silica gel gave 520mg (63%) of the product. 1H NMR (200 MHz, CDCl3): 257 (dd; 4,8 Hz; 2H), 2.81 (dd; 7, 13 Hz; 1H), 3.13 (dd; 8, 14 Hz; 1H), 3.63 (dt; 14, 7 Hz; 1H), 3.74 (s, 3H), 6.82 (d, 8 Hz, 2H), 7.02 (d, 8 Hz, 1H), 7.14-7.34 (m, 5H), 8.03 (br s, 1H). FAB-MS: calculated for C17H17NO2 267; found 267 (100%).

Workup

  1. temperaturethe resulting mixture refluxed in an oil bath under a nitrogen atmosphere for 20 hours
  2. washThe organic layer was washed with 1N HCl (3×50 mL) and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b8b6871bb62140949058600f10f3ad51
Source dataset
uspto-grants-1994_05
Patent number
US05317017

Reaction notes

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