Dabco → HCID 178439362, compound

HRID 2117115Notes

Reaction equation

HRID 2117115 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 (2mL), 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-922b27c47f0a42a9bafd7d2051910238
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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