Pyridine → HCID 86670034, compound

HRID 1520175Notes

Reaction equation

HRID 1520175 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, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(6-fluoro-3,4-dihydroquinolin-1(2H)-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (150 mg, 0.43 mmol) in dichloromethane (30 mL) was added pyridine (136 mg, 1.72 mmol) and then Tf2O (243 mg, 0.86 mmol) was added dropwise with stifling at 0° C. The resulting solution was stirred for 4 h at room temperature and then washed with water (3×50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford methyl 3-(6-fluoro-3,4-dihydroquinolin-1(2H)-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate as red oil (200 mg, crude).

Workup

  1. customwith stifling at 0° C
  2. washwashed with water (3×50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17752c952eae4220b31e68be64cf6398
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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