Hydrochloric Acid → 7-bromo-2-fluoro-5-methylene-3-(trimethylsilyl)-5H-chromeno[2,3-b]pyridine

HRID 335823Notes

Reaction equation

HRID 335823 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:18](=[CH:19][CH:20]=1)[O:17][C:7]1=[N:8][C:9]([F:16])=[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=[C:6]1[C:5]2=O.[CH3:22][Mg]Br.Cl.CCOC(C)=O>C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:18](=[CH:19][CH:20]=1)[O:17][C:7]1=[N:8][C:9]([F:16])=[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=[C:6]1[C:5]2=[CH2:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 67383508HCID 67383508, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 673832857-bromo-2-fluoro-5-methylene-3-(trimethylsilyl)-5H-chromeno[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-bromo-2-fluoro-3-(trimethylsilyl)-5H-chromeno[2,3-b]pyridin-5-one (1.05 g, 2.9 mmol) was dissolved in dry THF (30 mL) and treated with methylmagnesium bromide (3.0 M in diethyl ether, 2.0 mL, 6.00 mmol). After 15 minutes 5N HCl (30 mL) was added followed by EtOAc (100 mL) and water (100 mL). The phases were mixed and separated and the organics were dried with magnesium sulfate before evaporating to dryness under reduced pressure. Purification using silica chromatography (hexane to dichloromethane gradient) gave the desired 7-bromo-2-fluoro-5-methylene-3-(trimethylsilyl)-5H-chromeno[2,3-b]pyridine.

Workup

  1. additionThe phases were mixed
  2. customseparated
  3. dry with materialthe organics were dried with magnesium sulfate
  4. custombefore evaporating to dryness under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-38690b9b75dd4294a44f414aab2a9366
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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