Potassium Carbonate → HCID 86711935, compound

HRID 1475243Notes

Reaction equation

HRID 1475243 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[N:9][C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:13]=2)=[N:7]1.[CH2:31]([Sn](CCCC)(CCCC)C=C)[CH2:32]CC.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[CH:31]([C:2]1[CH:3]=[C:4]([CH2:5][N:6]2[C:10]([CH3:11])=[N:9][C:8]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:25])[F:26])=[CH:19][CH:18]=4)[N:13]=3)=[N:7]2)[CH:28]=[CH:29][CH:30]=1)=[CH2:32]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81998TributylvinyltinHCID 86711906HCID 86711906, compound

Product 1

HCID 86711935HCID 86711935, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 5-(1-(3-bromobenzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (Example 11, Step 1; 200 mg, 0.42 mmol), tributyl(vinyl)stannane (159 mg, 0.50 mmol) and K2CO3 (174 mg, 1.26 mmol) in 1,4-dioxane (5 mL), was added Pd(PPh4)3 (28 mg, 0.025 mmol). The reaction mixture was heated in a sealed vial at 110° C. under inert atmosphere for 12 h, cooled to RT, diluted with H2O (30 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with H2O (10 mL) and brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure; the residue was purified by prep-HPLC to give the title compound as a white solid; MS (ES+) C21H16F3N5O2 requires: 427. found: 428 [M+H]+; 1H-NMR (500 MHz, DMSO-d6) δ 8.22 (d, J=9 Hz, 2H), 7.61 (d, J=9 Hz, 2H), 7.48 (d, J=7 Hz, 1H), 7.43 (s, 1H), 7.38 (m, 1H), 7.21 (d, J=7 Hz, 1H), 6.76 (m, 1H), 5.87 (d, J=17.5 Hz, 1H), 5.57 (s, 2H), 5.31 (d, J=11.5 Hz, 1H), 2.60 (s, 3H).

Workup

  1. temperaturecooled to RT
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with H2O (10 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-4f09069823454ecf9a462de6f1204885
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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