Pyridine → HCID 86670034, compound

HRID 1520143Notes

Reaction equation

HRID 1520143 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[C:13](=[O:26])[NH:14][C:15]3[C:20]([N:21]=1)=[CH:19][C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=3)[CH2:7][CH2:6][CH2:5]2.N1C=CC=CC=1.[O:33](S(C(F)(F)F)(=O)=O)[S:34]([C:37]([F:40])([F:39])[F:38])(=O)=[O:35]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[C:13]([O:26][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:35])=[O:33])=[N:14][C:15]3[C:20]([N:21]=1)=[CH:19][C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=3)[CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 68194191HCID 68194191, compound

Product 1

HCID 86670034HCID 86670034, compoundYield 131.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(6-fluoro-1,2,3,4-tetrahydroquinolin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (150 mg, 0.43 mmol) in dichloromethane (40 mL) was added pyridine (136 mg, 1.72 mmol) and Tf2O (242 mg, 0.86 mmol) with stifling overnight maintained with an inert atmosphere of nitrogen at room temperature. The reaction was then quenched with water (50 mL), extracted with dichloromethane (3×10 mL), the organic layers combined and dried over anhydrous magnesium sulfate, concentrated under vacuum to afford methyl 3-(6-fluoro-1,2,3,4-tetrahydroquinolin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (274 mg, crude), which was used to the next step directly.

Workup

  1. customThe reaction was then quenched with water (50 mL)
  2. extractionextracted with dichloromethane (3×10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6fbaecabcc28441f8bc7ea61f3ec3132
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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