Methyl iodide → HCID 57438725, compound

HRID 2354508Notes

Reaction equation

HRID 2354508 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]([CH3:20])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[N:6][CH:7]=1.CI.[CH3:23][Si](C)(C)[N-][Si](C)(C)C.[K+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]([CH3:23])([CH3:20])[C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 57438724HCID 57438724, compound

Product 1

HCID 57438725HCID 57438725, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 2-(5-fluoro-2-pyridyloxy)propionate (2.9 g, 10 mmol) and methyl iodide (3.3 mL, 53 mmol) in 40 mL of anhydrous THF at −78° C. was added potassium hexamethyldisilazide (0.5 M in toluene, 32 mL, 16 mmol). The reaction was allowed to warm to room temperature over 3 h and was partitioned between saturated ammonium chloride (150 mL) and EtOAc (150 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×50 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness, and the residue was purified by flash column chromatography on silica gel eluted with 0 to 20% EtOAc in hexane to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.63 (d, 1H), 7.44 (ddd, 1H), 7.27 (m, 3H), 7.18 (m, 2H), 6.74 (dd, 1H), 5.09 (s, 2H) 1.64 (s, 6H). LC-MS: m/e 290 (M+H)+ (3.7 min).

Workup

  1. customwas partitioned between saturated ammonium chloride (150 mL) and EtOAc (150 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with EtOAc (2×50 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customthe residue was purified by flash column chromatography on silica gel
  8. washeluted with 0 to 20% EtOAc in hexane

Sources & evidence

ORD record
ord-b75a655a5aec4d76a56154e140042aa6
Source dataset
uspto-grants-2010_07
Patent number
US07754188B2

Reaction notes

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