Sodium Iodide → HCID 86703563, compound

HRID 1849692Notes

Reaction equation

HRID 1849692 reaction equation
[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]3([CH3:27])[CH2:25][CH2:24][C:23](=[CH2:26])[CH2:22][CH2:21]3)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][CH2:2]1.O1CCCC1.C[Si](C)(C)[C:35](F)([F:37])[F:36].[I-].[Na+]>C(OCC)(=O)C>[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]3([CH3:27])[CH2:25][CH2:24][C:23]4([C:35]([F:37])([F:36])[CH2:26]4)[CH2:22][CH2:21]3)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 5238Sodium Iodide2×HCID 8028TetrahydrofuranHCID 552549(Trifluoromethyl)trimethylsilane2×HCID 86703559HCID 86703559, compound

Product 1

HCID 86703563HCID 86703563, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

To a 10 mL microwave tube charged with tert-butyl 5-cyclopropyl-2-fluoro-4-((1-methyl-4-methylenecyclohexyl)methoxy)benzoate (0.475 g, 1.27 mmol) and tetrahydrofuran (4 mL) was added trimethyl(trifluoromethyl)silane (0.375 mL, 2.54 mmol) and sodium iodide (0.42 g, 2.79 mmol). The reaction mixture was heated at 115° C. for 1 hour. After cooling to ambient temperature, additional trimethyl(trifluoromethyl)silane (0.375 mL, 2.54 mmol) and sodium iodide (0.42 mg, 2.79 mmol) were added. The reaction was heated at 115° C. for another 1 hour. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate (30 mL) and washed with water. The aqueous layer was separated and extracted with ethyl acetate (3×30 mL). The combined organics were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography (0% to 5% ethyl acetate in hexanes) afforded the title compound (0.426 g, 79%) as a colorless oil: MS (ES+) m/z 369.1 (M−55).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. temperatureThe reaction was heated at 115° C. for another 1 hour
  3. temperatureAfter cooling to ambient temperature
  4. washwashed with water
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate (3×30 mL)
  7. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by column chromatography (0% to 5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-57b08de351f544659892e5ae00f1ed47
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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