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

HRID 1276288노트

반응식

HRID 1276288 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-6c504619f122429baa9be1747df81230
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166034

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