Ammonium Chloride → 2-Fluoro-N1-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yl)benzene-1,4-diamine

HRID 1711105Notes

Reaction equation

HRID 1711105 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]=[C:19]([C:21]3[N:22]=[CH:23][N:24]([CH3:26])[CH:25]=3)[S:20][C:13]=12.[NH4+].[Cl-]>CO.O.[Fe]>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]=[C:19]([C:21]3[N:22]=[CH:23][N:24]([CH3:26])[CH:25]=3)[S:20][C:13]=12

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 59457676HCID 59457676, compound

Product 1

HCID 594577422-Fluoro-N1-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yl)benzene-1,4-diamineYield 136.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of nitro compound 417 (370 mg, 1.00 mmol) in a mixture of MeOH (20 mL) and water (10 mL) were added iron powder (280 mg, 5.01 mmol) and NH4Cl (107 mg, 2.00 mmol). The reaction mixture was heated to reflux for 2 hrs, cooled to room temperature and filtered through celite. The filtrate was concentrated, diluted with minimal amount of methanol and treated with AcOEt/hexanes, to afford title compound 418 (463 mg, quantitative yield, ammonium salt) as a yellow solid. LCMS: 340.0 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hrs
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated
  5. additiondiluted with minimal amount of methanol
  6. additiontreated with AcOEt/hexanes

Sources & evidence

ORD record
ord-cd749d74a89e44f49c76f6b91194a9ee
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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