Tetrahydrofuran → HCID 67774107, compound

HRID 533428Notes

Reaction equation

HRID 533428 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[C:21]([C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[C:38]([C:41]([O:43][CH3:44])=[O:42])[CH:39]=3)[C:34]([F:45])=[CH:33][N:32]=2)=[N:22][CH:23]=[C:24]([F:30])[C:25]=1[Si](C)(C)C.C1COCC1>O>[F:19][C:20]1[C:21]([C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[C:38]([C:41]([O:43][CH3:44])=[O:42])[CH:39]=3)[C:34]([F:45])=[CH:33][N:32]=2)=[N:22][CH:23]=[C:24]([F:30])[CH:25]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 67775619HCID 67775619, compound

Product 1

HCID 67774107HCID 67774107, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tetrabutylammonium fluoride (1M THF solution, 0.35 mL) was added to a mixture of methyl 1-[3,5-difluoro-4-(trimethylsilyl)pyridin-2-yl]-4-fluoroisoquinoline-7-carboxylate and THF (1.8 mL), and stirred at room temperature overnight. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried, and concentrated under reduced pressure. The resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 1-(3,5-difluoropyridin-2-yl)-4-fluoroisoquinoline-7-carboxylate (55 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-01f0962942ba4a91ab10baec2e263023
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

Loading…