Sodium Carbonate → HCID 10118567, compound

HRID 2181304Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:32])[CH2:14][CH2:15][N:16]([C:18]2[CH:19]=[CH:20][C:21](OS(C(F)(F)F)(=O)=O)=[N:22][CH:23]=2)[CH3:17])=[CH:9][N:8]=1)(=O)=O.[CH3:35][O:36][C:37]1[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:38]=1B(O)O.[C:48](=[O:51])([O-])[O-].[Na+].[Na+]>[Cl-].[Na+].O>[CH3:35][O:36][C:37]1[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:38]=1[C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:32])[CH2:14][CH2:15][N:16]([C:18]2[CH:19]=[CH:20][C:21]([C:40]3[CH:41]=[CH:42][C:37]([O:36][CH3:35])=[CH:38][C:39]=3[O:51][CH3:48])=[N:22][CH:23]=2)[CH3:17])=[CH:9][N:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N,N′-bis(2-trifluoromethanesulfonyloxy-5-pyridyl)-N,N′-dimethylethylenediamine (108.0 mg, 0.200 mmol) synthesized in Reference Example 1 in ethanol-toluene (1:6, 3.5 mL) were added 2,4-dimethoxyphenylboronic acid (108.0 mg, 0.200 mmol), tetrakis-(triphenylphosphine)palladium (46.0 mg, 0.040 mmol) and a 2.0 M aqueous sodium carbonate solution (0.20 mL, 0.40 mmol). After stirring at 80° C. for 2 hours, brine was added, and the mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified column chromatography on silica gel to provide N,N′-bis[2-(2,4-dimethoxyphenyl)-5-pyridyl]-N,N′-dimethylethylenediamine as a colorless amorphous powder (109.0 mg; quantitative).

Workup

extractionthe mixture was extracted with chloroform
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified column chromatography on silica gel

Sources & evidence

ORD record: ord-4ddaf56589e9405fae4208ff95d39a45
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06890940B2

Reaction notes

Loading…