Dabco → HCID 178439362, compound

HRID 347509Notes

Reaction equation

HRID 347509 reaction equation
Cl[C:2]1[C:7]2=[C:8]([CH:11]([CH3:13])[CH3:12])[CH:9]=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[F:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[OH:24].C1N2CCN(CC2)C1>CC#N>[F:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[O:24][CH:2]1[C:7]2=[C:8]([CH:11]([CH3:13])[CH3:12])[CH:9]=[CH:10][N:6]2[N:5]=[CH:4][NH:3]1

Participants

5

Reactant 3

HCID 9237DabcoHCID 98252-Fluoro-4-nitrophenolHCID 210816774-Chloro-5-(propan-2-yl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 178439362HCID 178439362, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-chloro-5-isopropylpyrrolo[2,1-f][1,2,4]triazine (0.038 g, 0.194 mmol, 1.0 equiv) and 2-fluoro-4-nitrophenol (0.062 g, 0.388 mmol, 2.0 equiv) in anhydrous CH3CN (2 mL), stirred for five minutes under a nitrogen atmosphere then was added DABCO (0.044 g, 0.388 mmol, 2.0 equiv) and the reaction mixture was heated at 50° C. for 2 h. The mixture was cooled to room temperature and quenched with 1 N HCl. The solution was extracted with CH2Cl2 (3×30 ml), the combined organic extracts dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel (Merck KGaA, 230–400 mesh particle size) flash chromatography, eluting with 2/1 hexane/ethyl acetate, afforded the title compound (0.048 g, 79%). 1H NMR (CDCl3) δ 8.07–8.13 (m, 2H), 7.77 (s, 1H), 7.68–7.69 (m, 1H), 7.46–7.50 (m, 1H), 6.71–6.72 (m, 1H), 3.53–3.56 (m, 1H), 1.29–1.31 (m, 6H); HRMS(ESI), calc, 317.1050 (M+H)+ found, 317.1039.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with 1 N HCl
  3. extractionThe solution was extracted with CH2Cl2 (3×30 ml)
  4. dry with materialthe combined organic extracts dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel (Merck KGaA, 230–400 mesh particle size) flash chromatography
  8. washeluting with 2/1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-bcdcd87eab4949ca87904c150fdc1af2
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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