Potassium Carbonate → 1-ethyl-3,3,5-trimethyl-7-[3-(2-oxo-3-phenyl-2H-quinolin-1-yl)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 69061Notes

Reaction equation

HRID 69061 reaction equation
Br[C:2]1[C:3](=[O:34])[N:4]([CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:33]=[CH:32][C:19]3[N:20]([CH2:30][CH3:31])[C:21](=[O:29])[C:22]([CH3:28])([CH3:27])[C:23](=[O:26])[N:24]([CH3:25])[C:18]=3[CH:17]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O>[CH2:30]([N:20]1[C:21](=[O:29])[C:22]([CH3:28])([CH3:27])[C:23](=[O:26])[N:24]([CH3:25])[C:18]2[CH:17]=[C:16]([O:15][CH2:14][CH2:13][CH2:12][N:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:11]=[C:2]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:3]3=[O:34])[CH:33]=[CH:32][C:19]1=2)[CH3:31]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 669616127-[3-(3-bromo-2-oxo-2H-quinolin-1-yl)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 706567841-ethyl-3,3,5-trimethyl-7-[3-(2-oxo-3-phenyl-2H-quinolin-1-yl)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 68.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-[3-(3-Bromo-2-oxo-2H-quinolin-1-yl)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (0.5 g), phenylboronic acid (0.12 g), tetrakis(triphenyl phosphine)palladium (0) (0.11 g), and potassium carbonate (0.39 g) were added to dioxane (5 ml). The mixture was heated under reflux for 2 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature. Water was added thereto, followed by extraction by ethyl acetate. The organic layer was dried over sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1→3:1). The purified product was condensed to dryness under reduced pressure, thereby obtaining the title compound (0.34 g) as a white amorphous solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours under nitrogen atmosphere
  3. extractionfollowed by extraction by ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate, and condensed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1→3:1)
  6. customcondensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-9670221bed3940e18566d8a38d8e402a
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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