Ammonium Chloride → 3-Fluoro-4-(2-(5-((4-methylpiperazin-1-yl)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)aniline

HRID 2193787Notes

Reaction equation

HRID 2193787 reaction equation
[F:1][C:2]1[CH:31]=[C:30]([N+:32]([O-])=O)[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:16][N:15]=3)[S:13][C:6]=12.[NH4+].[Cl-]>[Fe].CCO.O>[F:1][C:2]1[CH:31]=[C:30]([CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]4)=[CH:16][N:15]=3)[S:13][C:6]=12)[NH2:32]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 594577107-(2-Fluoro-4-nitrophenoxy)-2-(5-((4-methylpiperazin-1-yl)methyl)pyridin-2-yl)thieno[3,2-b]pyridine

Product 1

HCID 594577213-Fluoro-4-(2-(5-((4-methylpiperazin-1-yl)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of 401 (306 mg, 0.64 mmol) and NH4Cl (30 mg, 0.54 mmol) in 2:1 EtOH/water (10.5 mL) was added iron powder (304 mg, 5.43 mmol) and the suspension was heated to reflux for 1 hour. The reaction mixture was filtered through celite and concentrated to provide title compound 396, that was used without further purification (343 mg, 100% yield). MS (m/z): (M+1) 450.0 (100%).

Workup

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

Sources & evidence

ORD record
ord-19ac366a1524491fa50a79140455c1e8
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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