Sodium Carbonate → HCID 11501024, compound

HRID 2172154Notes

Reaction equation

HRID 2172154 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([O:18]C)=[O:17])=[N:9]2)=[CH:4][CH:3]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([OH:18])=[O:17])=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 66616129HCID 66616129, compound

Product 1

HCID 11501024HCID 11501024, compoundYield 79.2%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

A 10 mL glass tube with a stirbar is charged with methyl 3-[1-(4-bromo-phenyl)-1H-[1,2,4]triazol-3-yl]-benzoate (265 mg, 0.74 mmol), benzeneboronic acid (90.2 mg, 0.74 mmol), sodium carbonate (235 mg), tetrabutylammonium iodide (273 mg), palladium acetate (0.8 mg) and 6 mL water. The vessel is sealed and placed into the reaction cavity of a microwave reactor. The reaction is performed with 60 W power at 150° C., with monitoring by LC/MS. After the reaction is determined to be complete, the mixture is filtered through celite and acidified using 1N HCl until the pH of the medium is less than 7. The resulting solid is collected by filtration and recrystallized to purity from THF-hexane to afford the title product (200 mg, 79%) as a white powder, m.p. 263-265° C. 1H NMR (300 MHz, DMSO-d6): δ 9.47 (1H, s), 8.69 (1H, s), 8.34 (1H, d, J=7.5 Hz), 8.05-7.39 (1H, m). MS (ES+): m/e 343 (30), 342 (100).

Workup

  1. customThe vessel is sealed
  2. customplaced into the reaction cavity of a microwave reactor
  3. customis performed with 60 W power at 150° C., with monitoring by LC/MS
  4. filtrationthe mixture is filtered through celite
  5. filtrationThe resulting solid is collected by filtration
  6. customrecrystallized to purity from THF-hexane

Sources & evidence

ORD record
ord-9bdc7f8977984fa599c889dc32706080
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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