Pyridine → HCID 22240462, compound

HRID 1064052Notes

Reaction equation

HRID 1064052 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:9]=[C:8]([C:19]([NH2:21])=O)[CH:7]=1.N1C=CC=CC=1.O1CCOCC1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(OCC)(=O)C.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:9]=[C:8]([C:19]#[N:21])[CH:7]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 312751,4-DioxaneHCID 22240457HCID 22240457, compound

Product 1

HCID 22240462HCID 22240462, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 5-(2-furyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxamide (2.0 g, 6.6 mmol) was added pyridine (1.6 mL, 20 mmol) and dioxane (66 mL). Trifluoroacetic anhydride (1.9 mL, 13 mmol) was added dropwise over 2 min, and the resulting suspension was stirred for 40 min. The now clear red solution was poured into water (70 mL) and ethyl acetate (70 mL). The layers were separated, and the organic layer was washed with 1N aqueous hydrochloric acid (2×50 mL), saturated aqueous sodium chloride, and dried over sodium sulfate. The organic layers were concentrated, and the resulting residue was purified by radial chromatography (20-80% ethyl acetate in hexanes) to afford 5-(2-furyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-carbonitrile (1.4 g, 74%) as an orange solid. LC/MS (ESI+): 266.0 (M+H)+. 1H NMR (CDCl3) δ 7.44 (br m, 1H), 7.34 (d, 2H), 7.01 (s, 1H), 7.00 (d, 2H), 6.34 (m, 1H), 5.92 (d, 1H), 3.85 (s, 3H).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with 1N aqueous hydrochloric acid (2×50 mL), saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationThe organic layers were concentrated
  5. customthe resulting residue was purified by radial chromatography (20-80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8d46e17d9d8d47dd9ca873381845e15b
Source dataset
uspto-grants-2005_11
Patent number
US06967208B2

Reaction notes

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