Tetrahydrofuran → 7-[4-(1-Ethyl-1-hydroxy-propyl)-[1,2,3]triazol-1-ylmethyl]-4-(3-fluoro-phenyl)-chromen-2-one

HRID 2422487Notes

Reaction equation

HRID 2422487 reaction equation
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[CH:10][C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[CH2:23]([C:25]([OH:30])([CH2:28][CH3:29])[C:26]#[CH:27])[CH3:24].C1COCC1>C(OCC)(=O)C.[Cu](I)I>[CH2:26]([C:25]([C:23]1[N:3]=[N:2][N:1]([CH2:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=4)=[CH:10][C:11](=[O:15])[O:12]3)=[CH:7][CH:6]=2)[CH:24]=1)([OH:30])[CH2:28][CH3:29])[CH3:27]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 226983-Ethyl-1-pentyn-3-olHCID 597748747-(azidomethyl)-4-(3-fluorophenyl)-2H-chromen-2-one

Product 1

HCID 250563657-[4-(1-Ethyl-1-hydroxy-propyl)-[1,2,3]triazol-1-ylmethyl]-4-(3-fluoro-phenyl)-chromen-2-one

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-(azidomethyl)-4-(3-fluorophenyl)-2H-chromen-2-one (343 mg, 0.78 mmol) and 3-ethyl-1-pentyn-3-ol (80 mg, 0.71 mmol) in THF (7 mL) N,N-diisopropylethylamine (622 uL, 3.6 mmol) and copper iodide (204 mg, 1.07 mmol) were added. After overnight stirring, the reaction was diluted with ethyl acetate, filtered and washed with water and brine. The organic layer was then dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (acetone/CH2Cl2 10:90) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 7.89 (s, 1H), 7.7-7.6 (m, 1H), 7.53 (d, 1H), 7.45-7.32 (m, 4H), 7.27 (d, 1H), 6.42 (s, 1H), 5.79 (s, 2H), 3.78 (s, 1H), 2.0-1.74 (m, 4H), 0.78 (t, 6H).

Workup

  1. filtrationfiltered
  2. washwashed with water and brine
  3. dry with materialThe organic layer was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue obtained
  7. customwas purified by column chromatography (acetone/CH2Cl2 10:90)

Sources & evidence

ORD record
ord-0694b45e958743cdb7865996d34083f8
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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