HCID 67383577, compound → HCID 67383508, compound

HRID 335822Notes

Reaction equation

HRID 335822 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[N:16]=[C:15]([F:17])[C:14]([Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:13][C:8]=2[C:9]([O:11]C)=O)=[C:4](I)[CH:3]=1.C([Mg]Cl)(C)C>C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:22][CH:23]=1)[O:6][C:7]1=[N:16][C:15]([F:17])=[C:14]([Si:18]([CH3:19])([CH3:21])[CH3:20])[CH:13]=[C:8]1[C:9]2=[O:11]

Participants

5

Reactant 2

HCID 67383577HCID 67383577, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 67383508HCID 67383508, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinate (2.04 g, 3.89 mmol) was dissolved in dry THF (80 mL) and cooled in a dry ice bath to −78° C. Isopropylmagnesium chloride (2.0 M solution in diethyl ether, 3.89 mL (7.78 mmol) was added and the solution stirred for 15 minutes. The mixture was removed from the cold bath and allowed to slowly warm to RT. Water (100 mL), saturated ammonium chloride (10 mL), and EtOAc (200 mL) were added and the phases mixed and separated. The organics were dried with magnesium sulfate and evaporated to dryness under reduced pressure. The crude was purified using silica chromatography (hexane to ethyl acetate gradient) to give 7-bromo-2-fluoro-3-(trimethylsilyl)-5H-chromeno[2,3-b]pyridin-5-one.

Workup

  1. customThe mixture was removed from the cold bath
  2. temperatureto slowly warm to RT
  3. additionWater (100 mL), saturated ammonium chloride (10 mL), and EtOAc (200 mL) were added
  4. additionthe phases mixed
  5. customseparated
  6. dry with materialThe organics were dried with magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customThe crude was purified

Sources & evidence

ORD record
ord-3aeb56580dbd4ba3bcab3adac29f6ab5
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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