Water → HCID 59424517, compound

HRID 418665Notes

Reaction equation

HRID 418665 reaction equation
[Br:1][C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=2[F:21])[CH:3]=1.[NH4+].[Cl-].O>CCO.[Fe]>[Br:1][C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[F:21])[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 594245212-Bromo-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 59424517HCID 59424517, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a mixture of compound 50 (1.0 g, 2.96 mmol) and NH4Cl (46 mg, 0.86 mmol) in EtOH (29 mL)/water (15 mL) at 100° C., Fe (1.4 g, 25.15 mmol) was added in one portion and the mixture was refluxed with vigorous stirring for 40 min. The mixture was filtered through Celite®, the Celite® washed with EtOH and the combined filtrate concentrated under reduced pressure. The residue was suspended in EtOAc, washed with water; the organic phase was dried over anhydrous Na2SO4 and evaporated affording title compound 225 (916.15 mg, 91% yield). MS (m/z): 338.9 (96%), 340.9 (100%).

Workup

  1. temperaturethe mixture was refluxed
  2. filtrationThe mixture was filtered through Celite®
  3. washthe Celite® washed with EtOH
  4. concentrationthe combined filtrate concentrated under reduced pressure
  5. washwashed with water
  6. dry with materialthe organic phase was dried over anhydrous Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-a5f61e25d5314b5898d29fa2c30a139d
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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