Nitrogen → HCID 86711497, compound

HRID 517556Notes

Reaction equation

HRID 517556 reaction equation
N#N.Br[C:4]1[CH:5]=[C:6]([CH:30]=[CH:31][CH:32]=1)[CH2:7][C:8]1[O:12][C:11]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[N:14]=2)=[N:10][C:9]=1[CH3:29].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[C:67]([O-])([O-:69])=[O:68].[Cs+].[Cs+].[CH3:73][N:74]1[CH2:79][CH2:78][NH:77][CH2:76][CH2:75]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[F:28][C:25]([F:26])([F:27])[C:67]([O-:69])=[O:68].[CH3:73][NH+:74]1[CH2:79][CH2:78][N:77]([C:4]2[CH:32]=[CH:31][CH:30]=[C:6]([CH2:7][C:8]3[O:12][C:11]([C:13]4[O:17][N:16]=[C:15]([C:18]5[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=5)[N:14]=4)=[N:10][C:9]=3[CH3:29])[CH:5]=2)[CH2:76][CH2:75]1

Participants

8

Reactant 5

HCID 947NitrogenHCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 73211791HCID 73211791, compound

Product 1

HCID 86711497HCID 86711497, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a vial under N2 containing 5-(5-(3-bromobenzyl)-4-methyloxazol-2-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (27 mg, 0.056 mmol), tris(dibenzylideneacetone)dipalladium (10 mg, 0.011 mmol), Xphos (11 mg, 0.022 mmol), and Cs2CO3 (37 mg, 0.11 mmol) was added dioxane (1 mL, degassed with N2) followed by 1-methylpiperazine (10 μL, 0.084 mmol). The vial was sealed and heated to 120° C. in a Biotage microwave reactor for 60 min. The mixture was cooled to room temperature, filtered (Celite), and concentrated under reduced pressure. The crude oil was purified by HPLC to provide an orange oil: (7.8 mg, 28%): 1H NMR (600 MHz, DMSO-d6) δ ppm 8.20 (d, J=8.8 Hz, 2H), 7.61 (d, J=8.4 Hz, 2H), 7.23 (t, J=8.0 Hz, 1H), 6.95 (s, 1H), 6.91 (app. dd, J=8.3 Hz, 2.4 Hz, 1H), 6.77 (d, J=7.5 Hz, 1H), 4.17 (s, 2H), 3.84 (d, J=13.6 Hz, 1H), 3.51 (d, J=12.0 Hz, 1H), 3.19-1.09 (m, 2H), 2.94 (t, J=12.6 Hz, 2H), 2.85 (s, 3H), 2.61 (app. t, J=1.9 Hz, 1H), 2.38 (app. t, J=1.9 Hz, 1H), 2.27 (s, 3H); MS (ES+) C25H24F3N5O3 requires: 499, found: 500 [M+H]+.

Workup

  1. customThe vial was sealed
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered (Celite)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude oil was purified by HPLC
  6. customto provide an orange oil

Sources & evidence

ORD record
ord-fdf93f9c593444468244ff8e6e7f19c6
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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