Iodine → 7-Bromo-1-fluoro-3-(neopentyloxy)spiro[chromeno[2,3-c]pyridine-5,2'-oxirane]

HRID 455701Notes

Reaction equation

HRID 455701 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:20](=[CH:21][CH:22]=1)[O:19][C:7]1[C:8]([F:18])=[N:9][C:10]([O:12][CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:11][C:6]=1[C:5]2=[CH2:23].O.II.C([O-])([O-])=[O:28].[K+].[K+]>C1COCC1.[Ag]=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]3([CH2:23][O:28]3)[C:6]3[CH:11]=[C:10]([O:12][CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[N:9]=[C:8]([F:18])[C:7]=3[O:19][C:20]2=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 807IodineHCID 962WaterHCID 11430Potassium CarbonateHCID 673829567-bromo-1-fluoro-5-methylene-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridine

Product 1

HCID 867619737-Bromo-1-fluoro-3-(neopentyloxy)spiro[chromeno[2,3-c]pyridine-5,2'-oxirane]Yield 96.4%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-bromo-1-fluoro-5-methylene-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridine (995 mg, 2.63 mmol) in THF (60 mL)/Water (10 mL) was added iodine (1335 mg, 5.26 mmol) and silver oxide (1219 mg, 5.26 mmol). The reaction mixture was allowed to stir at rt for 20 min. K2CO3 (545 mg, 3.95 mmol) was added in one portion and the reaction mixture was allowed to stir for 30 min. The reaction mixture was filtered through a pad of celite. The reaction mixture was partitioned between water and EtOAc. The organic phase was separated, dried over Na2SO4. The solvent was removed under reduced pressure to afford 7-bromo-1-fluoro-3-(neopentyloxy)spiro[chromeno[2,3-c]pyridine-5,2′-oxirane] as a yellow solid (1000 mg) which was taken onto the next step without further purification.

Workup

  1. stirringto stir for 30 min
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. customThe reaction mixture was partitioned between water and EtOAc
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4a13aafc805946368c57a775fc5318ea
Source dataset
uspto-grants-2013_07
Patent number
US08497264B2

Reaction notes

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