Ammonium Chloride → 3-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline

HRID 418736Notes

Reaction equation

HRID 418736 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([I:14])[S:13][C:6]=12.[NH4+].[Cl-]>[Fe].CCO.O>[F:1][C:2]1[CH:18]=[C:17]([CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([I:14])[S:13][C:6]=12)[NH2:19]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 594576617-(2-Fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine

Product 1

HCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of 399 (2 g, 4.81 mmol) and NH4Cl (220 mg, 4.08 mmol) in 2:1 EtOH/water (75 mL) was added iron powder (2.28 g, 40.8 mmol) and the suspension was heated to reflux for 1 hour. The reaction mixture was filtered through celite and concentrated to afford 410 (1.85 g, 100% yield), that was used without further purification MS. (m/z): (M+1) 386.8 (100%).

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-090bde8c8f3f48d783621c5398bd279f
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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