Quinoline → HCID 118549284, compound

HRID 1501307Notes

Reaction equation

HRID 1501307 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.Cl[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.FC(F)(F)S(O[C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[Si](C)(C)C)(=O)=O.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[C:15]1([CH:16]2[O:17][CH:2]3[CH:3]=[CH:4][C:5]4[C:10]([N:1]3[C:33]3[CH:32]=[CH:31][C:30]5[C:35]([C:34]2=3)=[CH:26][CH:27]=[CH:28][CH:29]=5)=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:18]=[CH:19][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 7047QuinolineHCID 77264-ChlorobenzaldehydeHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 12141975Methanesulfonic acid, trifluoro-, 2-(trimethylsilyl)-1-naphthalenyl ester

Product 1

HCID 118549284HCID 118549284, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure, treatment of quinoline (0.064 g, 59 μL, 0.50 mmol) and 4-chlorobenzaldehyde (0.105 g, 0.75 mmol) with 2-(trimethylsilyl)naphthalen-1-yl trifluoromethanesulfonate (0.209 g, 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=75/25) of the crude reaction mixture afforded 5-phenyl-5H,6aHnaphtho[2′,1′:4,5][1,3]oxazino[3,2-a]quinoline as a yellow solid (0.133 g, 67% 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-00068a6a4e004d37a548e4786605b3ec
Source dataset
uspto-grants-2015_12
Patent number
US09206196B1

Reaction notes

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