Water → 3-Fluoro-4-(2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridin-7-yloxy)aniline

HRID 1711095Notes

Reaction equation

HRID 1711095 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]([C:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH:19]=3)[S:13][C:6]=12.[NH4+].[Cl-].O>CCO.[Fe]>[F:1][C:2]1[CH:24]=[C:23]([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]([C:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH:19]=3)[S:13][C:6]=12)[NH2:25]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 594577227-(2-Fluoro-4-nitrophenoxy)-2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridine

Product 1

HCID 167179683-Fluoro-4-(2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridin-7-yloxy)anilineYield 67%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a mixture of nitro compound 379 (279 mg, 0.72 mmol) and NH4Cl (33 mg, 0.612 mmol) in EtOH (7.2 mL)/water (3.6 mL) at 100° C. Fe powder (342 mg, 6.2 mmol) was added in one portion and the mixture was heated to reflux with vigorous stirring for 40 min. The mixture was filtered through Celite®, the Celite® washed with EtOH and the combined filtrates were concentrated under reduced pressure. The residue was dissolved in MeOH and purified by flash chromatography (DCM/MeOH 5:1) providing 376 (171.3 mg, 0.48 mmol, 67% yield) as a yellow solid. LCMS:(M+H) 356.0.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. filtrationThe mixture was filtered through Celite®
  4. washthe Celite® washed with EtOH
  5. concentrationthe combined filtrates were concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in MeOH
  7. custompurified by flash chromatography (DCM/MeOH 5:1)

Sources & evidence

ORD record
ord-eb72f4f271ff49dab921a363ab67e542
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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