Lithium iodide → HCID 66685610, compound

HRID 1778400Notes

Reaction equation

HRID 1778400 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:22]([C:23]([O:25]C)=[O:24])=[C:21]2[C:16]([C:17]3[CH:30]=[CH:29][O:28][C:18]=3[C:19](=[O:27])[NH:20]2)=[CH:15][CH:14]=1)(=[O:11])=[O:10].[I-].[Li+]>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:22]([C:23]([OH:25])=[O:24])=[C:21]2[C:16]([C:17]3[CH:30]=[CH:29][O:28][C:18]=3[C:19](=[O:27])[NH:20]2)=[CH:15][CH:14]=1)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 66685239HCID 66685239, compound2×

Product 1

HCID 66685610HCID 66685610, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4-oxo-4,5-dihydrofuro[2,3-c]quinoline-6-carboxylate (Intermediate 87, 0.220 g) and lithium iodide (0.055 g) in pyridine (13 mL) was irradiated in the microwave at 150° C. for 30 minutes. After cooling, the mixture was concentrated in vacuo and the residue was suspended in 1M HCl. The solid was collected by filtration and triturated with acetone then dried under vacuum to give 7-(2-bromo-4-fluorobenzenesulfonylamino)-4-oxo-4,5-dihydro furo[2,3-c]quinoline-6-carboxylic acid (0.190 g) as a grey solid.

Workup

  1. customwas irradiated in the microwave at 150° C. for 30 minutes
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. filtrationThe solid was collected by filtration
  5. customtriturated with acetone
  6. customthen dried under vacuum

Sources & evidence

ORD record
ord-a7969ea3625c45e5882e73b0b2c26595
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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