HCID 67083247, compound → HCID 67083167, compound

HRID 2368672Notes

Reaction equation

HRID 2368672 reaction equation
[F:1][C:2]1[C:3]([CH:11]([OH:13])[CH3:12])=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]([CH3:10])[CH3:9]>C1(C)C=CC=CC=1.O=[Mn]=O>[F:1][C:2]1[C:3]([C:11](=[O:13])[CH3:12])=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]([CH3:10])[CH3:9]

Participants

4

Reactant 1

HCID 67083247HCID 67083247, compound

Product 1

HCID 67083167HCID 67083167, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

1-(3-Fluoro-4-isopropyl-pyridin-2-yl)-ethanol (prepared in the previous step, 3.00 g, 16.39 mmol) was dissolved in 60 mL of anhydrous toluene. MnO2 (4.05 g, 46.55 mmol) was added and the resulting mixture was stirred at 140° C. overnight. The mixture was then cooled to room temperature and filtered thought a pad of celite. The filtrate was concentrated and purified via MPLC (80 g, 0 to 20% ethyl acetate in hexane) to afford the title compound. Spectroscopic data: 1H-NMR (300 MHz, CDCl3): δ ppm 1.28 (d, J=6.73 Hz, 6 H), 2.70 (s, 3 H), 3.35 (hept, J=6.73 Hz, 1 H), 7.38 (dd, J=5.13 Hz, 1 H), 8.39 (d, J=4.69 Hz, 1 H).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified via MPLC (80 g, 0 to 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c399f7fb55c149cd96de2fbf4c36ec2e
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Reaction notes

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