Cesium carbonate → HCID 67502608, compound

HRID 921555Notes

Reaction equation

HRID 921555 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:9]=[C:10]([CH3:11])[C:3]=12.COC1C2C(=C3C(=CC=2)C(OC)=CC=N3)N=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:44]1([C:50]2[N:51]=[CH:52][NH:53][CH:54]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN1C(=O)CCC1.C(OCC)(=O)C.[Cu-]=O>[CH3:11][C:10]1[C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[N:53]2[CH:54]=[C:50]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[N:51]=[CH:52]2)[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:9]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 104622984,7-Dimethoxy-1,10-phenanthrolineHCID 67501017HCID 67501017, compoundHCID 178418822HCID 178418822, compound

Product 1

HCID 67502608HCID 67502608, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

Compound (97a) (2.00 g), copper(I) oxide (0.048 g), 4,7-dimethoxy-1,10-phenanthroline (0.243 g), cesium carbonate (3.07 g), polyethylene glycol (Mn=3400) (1.35 g), and 4-phenyl-1H-imidazole (1.17 g) were suspended in NMP, followed by stirring at 150° C. for 48 hr. The reaction solution was suspended in ethyl acetate, and insoluble matters were filtered through celite. The filtrate was washed with saturated saline and was then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate) to obtain compound (97b) (0.272 g, 10%) as a colorless oily substance.

Workup

  1. filtrationinsoluble matters were filtered through celite
  2. washThe filtrate was washed with saturated saline
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away
  5. customthe residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-37297495d83d4bab8f959a72f4f50289
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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