HCID 178472005, compound → HCID 19081629, compound

HRID 963426Notes

Reaction equation

HRID 963426 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8](=[CH:14][NH:15][C:16]([CH3:27])([CH3:26])[CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[C:4](Cl)[CH:3]=1>CS(C)=O.O>[Br:1][C:2]1[CH:29]=[C:28]2[C:5]([C:6](=[O:7])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][N:15]2[C:16]([CH3:27])([CH3:26])[CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 178472005HCID 178472005, compound

Product 1

HCID 19081629HCID 19081629, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

13bm) 4.3 g of ethyl 2-(4-bromo-2-chloro-benzoyl)-3-[2-(tert.-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethylamino]-acrylate (Example 13bl)) were dissolved in 40 ml of dimethyl sulphoxide under argon, treated with 1.1 g of potassium tert.-butylate and stirred for 15 min. Then, the mixture was stirred at 50° for 1.5 hrs. After cooling the mixture was diluted with 200 ml of water and the product was then extracted with two 200 ml portions of ethyl acetate, purified by silica gel chromatography in hexane/ethyl acetate 1:1 and crystallized from 30 ml of hexane/ethyl acetate 1:1. 2.45 g (62%) of ethyl 7-bromo-1-[2-(tert.-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-4-oxo-1,4-dihydro-quinoline-3-carboxylate were obtained as white crystals. M.p. 133° C.

Workup

  1. stirringThen, the mixture was stirred at 50° for 1.5 hrs
  2. temperatureAfter cooling the mixture
  3. extractionthe product was then extracted with two 200 ml portions of ethyl acetate
  4. custompurified by silica gel chromatography in hexane/ethyl acetate 1:1
  5. customcrystallized from 30 ml of hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-e9200a2a59c5443c8ec6b723b9ef50eb
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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