4-Fluorophenyl isocyanate → HCID 22480350, compound

HRID 1353675Notes

Reaction equation

HRID 1353675 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[N:10](OCCOC)[N:9]=2)=[CH:4][CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:31]([NH:30][C:27]4[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=4)=[O:32])[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 57440918HCID 57440918, compound

Product 1

HCID 22480350HCID 22480350, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-(4-fluorophenyl)-1-(2-methoxyethoxy)-1H-indazole-5-ylamine (115 mg, 0.36 mmol) in dioxane (5 mL) was added 4-fluorophenyl isocyanate (50 μL, 0.44 mmol). The reaction was stirred overnight at room temperature. It was then 35 filtered and the solid dried in a vacuum oven. The solid was then taken up in 6N HCl (10 mL) and methanol (10 mL) and heated to 80° C. for 2 hours. The reaction was then cooled to room temperature and quenched with NaHCO3 (100 mL) and extracted with ethyl acetate (3×40 mL). The organic layers were combined and dried with magnesium sulfate (MgSO4) and concentrated to a solid to afford the title compound (25 mg, 19% yield). 1H NMR (CDCl3) δ 13.1 (br s, 1H), 9.32 (s, 2H), 8.28 (s, 1H), 7.94 (dd, 2H), 7.52 (d, 1H), 7.48 (dd, 2H), 7.38 (t, 2H), 7.33 (dd, 1H), 7.11 (t, 2H); ES-MS (m/z) 364 [M+1]+.

Workup

  1. filtration35 filtered
  2. customthe solid dried in a vacuum oven
  3. temperaturemethanol (10 mL) and heated to 80° C. for 2 hours
  4. temperatureThe reaction was then cooled to room temperature
  5. customquenched with NaHCO3 (100 mL)
  6. extractionextracted with ethyl acetate (3×40 mL)
  7. dry with materialdried with magnesium sulfate (MgSO4)
  8. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-9df8553ac43248b4ab36b67484aa07e9
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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