Ammonium Chloride → 3-Fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine

HRID 347487Notes

Reaction equation

HRID 347487 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:14])[CH:12]=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1.[Cl-].[NH4+]>CO.O1CCCC1.[Zn]>[F:1][C:2]1[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:14])[CH:12]=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 210816494-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 210816133-Fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamineYield 92.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a heterogeneous mixture of 4-(2-fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazine (3.04 g, 10.55 mmol) in anhydrous methanol (60 mL) and anhydrous tetrahydrofuran (40 mL), at ambient temperature under nitrogen atmosphere, was added zinc dust (6.90 g, 105 mmol) and ammonium chloride (5.64 g, 105 mmol). The mixture was stirred for 7 h before the catalyst was filtered off and the filtrate was concentrated in vacuo to a pale yellow solid which was partitioned between chloroform and water. The aqueous layer was then extracted twice with chloroform. The combined chloroform layers were washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the title compound (2.51 g, 92%) as a solid. 1H NMR (CDCl3) δ 7.86 (s, 1H), 7.64 (d, 1H, J=2.6 Hz); 7.08–7.03 (m, 1H), 6.61 (d, 1H, J=2.4 Hz), 6.55–6.45 (m, 2H), 3.78 (s, 2H), 2.60 (s, 3H); HRMS(ESI), 259.0995 (M+H)+ calc, 259.0997 (M+H)+ found.

Workup

  1. filtrationwas filtered off
  2. concentrationthe filtrate was concentrated in vacuo to a pale yellow solid which
  3. customwas partitioned between chloroform and water
  4. extractionThe aqueous layer was then extracted twice with chloroform
  5. washThe combined chloroform layers were washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73d8b695bda44b9c9f1d02d6f99ea616
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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