Ammonium Chloride → 4-(2-(5-((Dimethylamino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline

HRID 2193789Notes

Reaction equation

HRID 2193789 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([N+:28]([O-])=O)[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][N:21]([CH3:23])[CH3:22])=[CH:16][CH:15]=3)[S:13][C:6]=12.[NH4+].[Cl-]>[Fe].CCO.O>[CH3:23][N:21]([CH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]2[S:13][C:6]3[C:7](=[N:8][CH:9]=[CH:10][C:5]=3[O:4][C:3]3[CH:24]=[CH:25][C:26]([NH2:28])=[CH:27][C:2]=3[F:1])[CH:11]=2)=[N:19][CH:18]=1)[CH3:22]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 587903851-(6-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)-N,N-dimethylmethanamine

Product 1

HCID 587903394-(2-(5-((Dimethylamino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroanilineYield 123.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of 402 (308 mg, 0.72 mmol) and NH4Cl (33 mg, 061 mmol) in 2:1 EtOH/water (9 mL) was added iron powder (345 mg, 6.17 mmol) and the suspension was heated to reflux for 1 hour. The reaction mixture was filtered through celite and concentrated to provide title compound 397 (350 mg, quantitative yield), that was used without further purification. MS (m/z): (M+1) 395.1 (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-1683933d1bc44dc7b0e9fec85ad339e1
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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