Ammonium Chloride → 3-Fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine

HRID 2117079Notes

Reaction equation

HRID 2117079 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[C:10]2=[CH:11][CH:12]=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1.[Cl-].[NH4+]>O1CCCC1.CO.[Zn]>[F:1][C:2]1[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[C:10]2=[CH:11][CH:12]=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1

Participants

6

Reactant 2

HCID 25517Ammonium Chloride2×HCID 210816564-(2-Fluoro-4-nitrophenoxy)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 210816213-Fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamineYield 92.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-fluoro-4-nitrophenoxy)pyrrolo[2,1-f][1,2,4]triazine (4.25 g, 15.5 mmol) in 40 mL of tetrahydrofuran and 60 mL of methanol at 0° C. was added zinc dust (3.04 g, 46.5 mmol, <10 micron) followed by ammonium chloride (2.49 g, 46.5 mmol). The mixture was stirred at room temperature overnight. Additional zinc dust (6.08 g, 93 mmol) and ammonium chloride (5.0 g, 93 mmol) were added and the reaction was allowed to stir at room temperature for 4 h. The heterogeneous mixture was filtered through a thin pad of Celite® with methanol and the filtrate was concentrated in vacuo. Purification by flash chromatography on silica gel (SiO2, EtOAc/Hexane 1:1) gave the title compound (3.5 g, 92%) as a yellow foam.

Workup

  1. stirringto stir at room temperature for 4 h
  2. filtrationThe heterogeneous mixture was filtered through a thin pad of Celite® with methanol
  3. concentrationthe filtrate was concentrated in vacuo
  4. customPurification by flash chromatography on silica gel (SiO2, EtOAc/Hexane 1:1)

Sources & evidence

ORD record
ord-98b0392fc7c54bcc88ebc4fc8e06a41a
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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