Pyridine → HCID 88868075, compound

HRID 1520189Notes

Reaction equation

HRID 1520189 reaction equation
[O:1]1[C:5]2=[CH:6][C:7]3[CH2:8][CH2:9][CH2:10][N:11]([C:14]4[C:15](=[O:28])[NH:16][C:17]5[C:22]([N:23]=4)=[CH:21][C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=5)[C:12]=3[CH:13]=[C:4]2[O:3][CH2:2]1.N1C=CC=CC=1.[O:35](S(C(F)(F)F)(=O)=O)[S:36]([C:39]([F:42])([F:41])[F:40])(=O)=[O:37]>ClCCl>[O:1]1[C:5]2=[CH:6][C:7]3[CH2:8][CH2:9][CH2:10][N:11]([C:14]4[C:15]([O:28][S:36]([C:39]([F:42])([F:41])[F:40])(=[O:37])=[O:35])=[N:16][C:17]5[C:22]([N:23]=4)=[CH:21][C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=5)[C:12]=3[CH:13]=[C:4]2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 68194088HCID 68194088, compound

Product 1

HCID 88868075HCID 88868075, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-[2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]quinolin-5-yl]-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (140 mg, 0.37 mmol) in dichloromethane (80 ml) was added pyridine (175 mg, 2.21 mmol) and Tf2O (510 mg, 1.81 mmol). The reaction was stirred overnight under atmosphere of nitrogen at room temperature. Then the reaction mixture was quenched with water (200 ml), extracted with dichloromethane (3×20 ml), the organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford methyl 3-(7,8-dihydro-[1,3]dioxolo[4,5-g]quinolin-5(6H)-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate as a red oil (150 mg, crude), which was used directly in the next step.

Workup

  1. customThen the reaction mixture was quenched with water (200 ml)
  2. extractionextracted with dichloromethane (3×20 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12b2d61c716248f3ab730602751fb984
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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