2-Fluoro-4-nitrophenol → 4-(2-Fluoro-4-nitrophenoxy)pyrrolo[2,1-f][1,2,4]triazine

HRID 347475Notes

Reaction equation

HRID 347475 reaction equation
Cl[C:2]1[C:7]2=[CH:8][CH:9]=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[F:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[OH:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[O:21][C:2]1[C:7]2=[CH:8][CH:9]=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 210816834-Chloropyrrolo(2,1-f)(1,2,4)triazine

Product 1

HCID 210816564-(2-Fluoro-4-nitrophenoxy)pyrrolo[2,1-f][1,2,4]triazineYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloropyrrolo[2,1-f][1,2,4]triazine (4.1 g, 27 mmol), 2-fluoro-4-nitrophenol (5.0 g, 32 mmol), and potassium carbonate (7.4 g, 53 mmol) in 100 mL of dimethylformamide was stirred at 60° C. for 15 h. After cooling to room temperature, the reaction mixture was filtered through a plug of silica gel with EtOAc. The filtrate was concentrated in vacuo and the resulting crude product was purified by flash chromatography on silica gel (SiO2, EtOAc/Hexane 1:4) to give the title compound (4.25 g, 58%) as a white solid. 1H NMR (CDCl3) δ 8.09 (m, 2H), 7.88 (s, 1H), 7.77 (dd, 1H, J=2.6, 1.2 Hz), 7.46 (t, 1H, J=7.6 Hz), 6.98 (dd, 1H, J=4.6, 1.4 Hz), 6.84 (dd, 1H, J=4.5, 2.6 Hz); 13C NMR (CDCl3) δ 160.6, 154.3 (J=254 Hz), 146.5, 145.8, 144.8 (J=12.9 Hz), 125.0, 121.7, 120.7, 114.5, 113.9, 113.6 (J=23.2 Hz), 103.6.

Workup

  1. filtrationthe reaction mixture was filtered through a plug of silica gel with EtOAc
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting crude product was purified by flash chromatography on silica gel (SiO2, EtOAc/Hexane 1:4)

Sources & evidence

ORD record
ord-42f1aee8f8bf4bb783e6c62296402dd0
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

Loading…