HCID 67083247, compound → HCID 67083167, compound

HRID 1892246Notes

Reaction equation

HRID 1892246 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-b85e81d2b8484d9db4253647899f9817
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Reaction notes

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