Isoquinoline → HCID 118549307, compound

HRID 1501312Notes

Reaction equation

HRID 1501312 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[Br:11][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[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Si](C)(C)C)(=O)=O.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[O:17][CH:1]3[C:10]4[C:5]([CH:4]=[CH:3][N:2]3[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]2=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 8405IsoquinolineHCID 2855718-Crown-6HCID 707414-BromobenzaldehydeHCID 522689Potassium FluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonate

Product 1

HCID 118549307HCID 118549307, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure, treatment of isoquinoline (0.129 g, 120 μL, 1.0 mmol) and 4-bromobenzaldehyde (0.278 g, 1.5 mmol) with 2-(trimethylsilyl)phenyl trifluoro-methane sulfonate (0.308 g, 292 μL, 1.2 mmol) in the presence of KF (0.140 g, 2.4 mmol) and 18-crown-6 (0.634 g, 2.4 mmol) in THF (4.0 mL) at −10° C. to room temperature for 12 hrs followed by flash column chromatography (Pet. ether/EtOAc=93/07) of the crude reaction mixture afforded 6-(4-bromophenyl)-4bH,6H-benzo[4,5][1,3]oxazino[2,3-a]isoquinoline as inseparable mixture of diastereomers as a yellow solid (0.314 g, 82% yield, dr determined by 1H NMR analysis of crude reaction mixture is 3:2).

Workup

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

Sources & evidence

ORD record
ord-b37f5e48785f4f14939c26270650bf1d
Source dataset
uspto-grants-2015_12
Patent number
US09206196B1

Reaction notes

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