Water → (Z)-4-(2-(4-(Dimethylamino)but-1-enyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline

HRID 418671Notes

Reaction equation

HRID 418671 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([CH:14]=[CH:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[S:13][C:6]=12.[NH4+].[Cl-].O>CCO.[Fe]>[CH3:20][N:18]([CH3:19])[CH2:17][CH2:16]/[CH:15]=[CH:14]\[C:12]1[S:13][C:6]2[C:7](=[N:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]2[CH:21]=[CH:22][C:23]([NH2:25])=[CH:24][C:2]=2[F:1])[CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 66649106HCID 66649106, compound

Product 1

HCID 58790344(Z)-4-(2-(4-(Dimethylamino)but-1-enyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroanilineYield 69%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 4-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-N,N-dimethylbut-3-en-1-amine (234) (171 mg, 0.44 mmol) and NH4Cl (20 mg, 0.37 mmol) in EtOH (4.4 mL)/water (2.2 mL) at 100° C., Fe (209 mg, 3.75 mmol) was added in one portion and the mixture was heated to reflux with vigorous stirring for 40 min. The mixture was filtered through Celiteg, the Celite® washed with EtOH and the combined organic solutions concentrated under reduced pressure. The residue was dissolved in MeOH and purified by preparative HPLC (gradient 40% to 95% MeOH in water, 45 min) giving title compound 235 as a yellow solid (122.8 mg, 0.3 mmol, 69% yield). MS (m/z): (M+1) 358.1 (100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. filtrationThe mixture was filtered through Celiteg
  4. washthe Celite® washed with EtOH
  5. concentrationthe combined organic solutions concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in MeOH
  7. custompurified by preparative HPLC (gradient 40% to 95% MeOH in water, 45 min)

Sources & evidence

ORD record
ord-7e1bcd06ce12459a89b4567516e4c300
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

Loading…