Sodium Carbonate → 1-(4-Carboxyphenyl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)naphthalene

HRID 1276288Notes

Reaction equation

HRID 1276288 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]1[O:13][C:14]([CH3:17])=[N:15][N:16]=1.[C:18]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)([OH:20])=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O>[C:18]([C:21]1[CH:26]=[CH:25][C:24]([C:2]2[C:3]3[C:8](=[C:7]([C:12]4[O:13][C:14]([CH3:17])=[N:15][N:16]=4)[CH:6]=[CH:5][CH:4]=3)[CH:9]=[CH:10][CH:11]=2)=[CH:23][CH:22]=1)([OH:20])=[O:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 221158772-(5-Bromo-1-naphthyl)-5-methyl-1,3,4-oxadiazole

Product 1

HCID 221158831-(4-Carboxyphenyl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)naphthalene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-(5-Bromo-1-naphthyl)-5-methyl-1,3,4-oxadiazole (D3) (1.50 g, 5.2 mmol) and 4-carboxyphenylboronic acid (0.86 g, 5.2 mmol) were stirred in dimethoxyethane (DME) (40 ml), and sodium carbonate (2.5 g, 23 mmol) in water (40 ml) was added. The mixture was purged by a stream of Ar for 15 min, when tetrakis (triphenylphosphine)palladium (0) (0.1 g, 0.008 mmol) was added. The mixture was stirred at reflux under Ar for 20 h, and then evaporated to remove DME. The grey suspension was acidified (5M HCl), and the solid was filtered off and dried in vacuo at 60° C. This material was heated at reflux in ethanol (30 ml), and filtered hot. The white solid so collected was dried in vacuo at 60° C. giving 1.32 (77%) of the title compound.

Workup

  1. customThe mixture was purged by a stream of Ar for 15 min
  2. temperatureat reflux under Ar for 20 h
  3. customevaporated
  4. customto remove DME
  5. filtrationthe solid was filtered off
  6. customdried in vacuo at 60° C
  7. temperatureThis material was heated
  8. temperatureat reflux in ethanol (30 ml)
  9. filtrationfiltered hot
  10. customThe white solid so collected
  11. customwas dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-6c504619f122429baa9be1747df81230
Source dataset
uspto-grants-2000_12
Patent number
US06166034

Reaction notes

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