Potassium Fluoride → 6-(1,4-Dioxaspiro[4.5]decan-8-yl)-5-methylpyridin-3-amine

HRID 1748537Notes

Reaction equation

HRID 1748537 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[N:16]=[CH:15][C:14]([N:17]=C(C4C=CC=CC=4)C4C=CC=CC=4)=[CH:13][C:12]=3[CH3:31])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[F-].[K+]>O1CCCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[N:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=3[CH3:31])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 522689Potassium FluorideHCID 866924886-(1,4-dioxaspiro[4.5]decan-8-yl)-N-(diphenylmethylene)-5-methylpyridin-3-amine

Product 1

HCID 866924896-(1,4-Dioxaspiro[4.5]decan-8-yl)-5-methylpyridin-3-amineYield 74.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(1,4-dioxaspiro[4.5]decan-8-yl)-N-(diphenylmethylene)-5-methylpyridin-3-amine (2.87 g), palladium acetate (314 mg) and potassium fluoride (1.63 g) in tetrahydrofuran (35 ml) and water (16 ml) was slowly added dropwise polymethylhydrosiloxane (PMHS) (1.67 ml) at room temperature with stirring, and then stirred at room temperature for 5 hours. During that time, polymethylhydrosiloxane (PMHS) (1.67 ml) was added twice. After completion of the reaction, water was added thereto, the mixture was extracted with chloroform, the organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained residue was purified with silica gel column chromatography (chloroform/methanol) to give the titled compound (1.28 g) as a gray solid. MS (ESI) m/z: 249 (M+H)+.

Workup

  1. stirringstirred at room temperature for 5 hours
  2. additionwas added
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe obtained residue was purified with silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-008588ee6a484c80956283f51390e7a9
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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