Quinoline → HCID 118549293, compound

HRID 1501300Notes

Reaction equation

HRID 1501300 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.[S:11]1[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12]1.FC(F)(F)S(O[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Si](C)(C)C)(=O)=O.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[S:11]1[CH:15]=[CH:14][C:13]([CH:16]2[O:17][CH:2]3[CH:3]=[CH:4][C:5]4[C:10]([N:1]3[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]2=3)=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:12]1

Participants

7

Reactant 5

HCID 7047QuinolineHCID 2855718-Crown-6HCID 681353-ThiophenecarboxaldehydeHCID 522689Potassium FluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonate

Product 1

HCID 118549293HCID 118549293, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure, treatment of quinoline (0.064 g, 59 μL, 0.50 mmol) and 3-Thiophenecarboxaldehyde (0.084 g, 66 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=75/25) of the crude reaction mixture afforded 5-(thiophen-3-yl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline as inseparable mixture of diastereomers as a yellow solid (0.109 g, 69% yield, dr determined by 1H NMR analysis of crude reaction mixture is 1:1).

Workup

  1. customof the crude reaction mixture

Sources & evidence

ORD record
ord-9ccc5c0c85f549c29f98ea7157b4ace6
Source dataset
uspto-grants-2015_12
Patent number
US09206196B1

Reaction notes

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