Ammonium Chloride → 3-fluoro-4-(2-(1-(methoxymethyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)aniline

HRID 418624Notes

Reaction equation

HRID 418624 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][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:15]=[CH:16][N:17]([CH2:19][O:20][CH3:21])[CH:18]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CCO.O.[Fe]>[F:1][C:2]1[CH:25]=[C:24]([CH:23]=[CH:22][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:15]=[CH:16][N:17]([CH2:19][O:20][CH3:21])[CH:18]=3)[S:13][C:6]=12)[NH2:26]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 587902607-(2-Fluoro-4-nitrophenoxy)-2-(1-(methoxymethyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridine

Product 1

HCID 587902243-fluoro-4-(2-(1-(methoxymethyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)anilineYield 100%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 94 (132 mg, 0.33 mmol) in EtOH (7 ml) and water (3 ml) was added ammonium chloride (16 mg, 0.9 eq, 0.3 mmol) and Fe (157 mg, 8.5 eq, 0.28 mmol) and the reaction mixture was heated to reflux for 2 hours. The reaction mixture was cooled to RT, filtered through celite then concentrated. The mixture was partitioned between DCM/water and the DCM was collected, dried over anhydrous sodium sulfate, filtered and concentrated. Crude 95 was used directly in the next step (122 mg, 100% yield). MS (m/z): 371.1 (M+H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationfiltered through celite
  4. concentrationthen concentrated
  5. customThe mixture was partitioned between DCM/water
  6. customthe DCM was collected
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8628a0f6e551452db7e9a96189f1050b
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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