Water → HCID 59457670, compound

HRID 418686Notes

Reaction equation

HRID 418686 reaction equation
[F:1][C:2]1[CH:26]=[C:25]([N+:27]([O-])=O)[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH3:21])[CH2:16][CH:15]=3)[S:13][C:6]=12.[NH4+].[Cl-].O>CCO.[Fe]>[NH2:27][C:25]1[CH:24]=[CH:23][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH3:21])[CH2:16][CH:15]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:26]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 59457690HCID 59457690, compound

Product 1

HCID 59457670HCID 59457670, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 1-(4-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone (269) (358.2 mg, 0.87 mmol) and NH4Cl (39.4 mg, 0.74 mmol) in EtOH (8.7 mL)/water (4.3 mL) at 100° C. was added Fe (411.3 mg, 7.36 mmol) in one portion and the mixture heated to reflux with vigorous stirring for 40 min. The mixture was filtered through Celite®, the Celite® washed with EtOH and the combined organic solutions concentrated under reduced pressure. The residue was dissolved in DCM, extracted with water, dried aver anhydrous Na2SO4 and concentrated under reduced pressure affording 270 (256.5 mg, 0.67 mmol, 77% yield) as a white solid. MS (m/z): (M+1) 384.2 (100%).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux
  3. filtrationThe mixture was filtered through Celite®
  4. washthe Celite® washed with EtOH
  5. concentrationthe combined organic solutions concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in DCM
  7. extractionextracted with water
  8. dry with materialdried aver anhydrous Na2SO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f35b9d258f1448b18315a592b16e761f
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

Loading…