Quinoline → HCID 118549306, compound

HRID 1501310Notes

Reaction equation

HRID 1501310 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[O:11]=[C:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14].FC(F)(F)S(O[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[Si](C)(C)C)(=O)=O.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[C:18]1([C:12]2([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:11][CH:2]3[CH:3]=[CH:4][C:5]4[C:10]([N:1]3[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]2=3)=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 7047QuinolineHCID 15349Ethyl benzoylformateHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonate

Product 1

HCID 118549306HCID 118549306, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure, treatment of quinoline (0.064 g, 59 μL, 0.50 mmol) and ethyl 2-oxo-2-phenylacetate (0.134 g, 119 μL, 0.75 mmol) with 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (0.179 g, 146 μL, 0.60 mmol) in the presence of KF (0.070 g, 1.2 mmol) and 18-crown-6 (0.317 g, 1.2 mmol) in THF (2.0 mL) at −10° C. to room temperature for 12 hrs followed by flash column chromatography (Pet. ether/EtOAc=90/10) of the crude reaction mixture afforded ethyl 5-phenyl-5H,6aHbenzo[4,5][1,3]oxazino[3,2-a]quinoline-5-carboxylate as a white solid (0.147 g, 77% yield, dr determined by 1H NMR analysis of crude reaction mixture is >20:1).

Workup

  1. customat −10° C. to room temperature
  2. customfor 12 hrs
  3. customreaction mixture

Sources & evidence

ORD record
ord-6f0d3c6c286040e79ef79db3ac678d39
Source dataset
uspto-grants-2015_12
Patent number
US09206196B1

Reaction notes

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