Ammonium Chloride → 7-(4-amino-2-fluorophenoxy)-N-(3-methoxyphenyl)thieno[3,2-b]pyridin-2-amine

HRID 418735Notes

Reaction equation

HRID 418735 reaction equation
[F:1][C:2]1[CH:26]=[C:25]([N+:27]([O-])=O)[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[S:13][C:6]=12.[NH4+].[Cl-]>[Fe].CCO.O>[NH2:27][C:25]1[CH:24]=[CH:23][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([NH:14][C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:26]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 594576847-(2-fluoro-4-nitrophenoxy)-N-(3-methoxyphenyl)thieno[3,2-b]pyridin-2-amine

Product 1

HCID 594577377-(4-amino-2-fluorophenoxy)-N-(3-methoxyphenyl)thieno[3,2-b]pyridin-2-amineYield 74%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of 403 (408 mg, 0.99 mmol) and NH4Cl (45 mg, 084 mmol) in 2:1 EtOH/water (15 mL) was added iron powder (472 mg, 8.43 mmol) and the suspension was heated to reflux for 1 hour. The reaction mixture was filtered through celite and concentrated to provide 404 (278 mg, 74% yield), that was used without further purification. MS (m/z): (M+1) 382.0 (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-5e7b954da9fc4cc8bb9fcf4826873540
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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