(6-Fluoropyridin-3-yl)(4-(methylthio)phenyl)methanol → (6-Fluoropyridin-3-yl)(4-(methylthio)phenyl)methanone

HRID 1811995

Reaction equation

HRID 1811995 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)[OH:9])=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 59548286(6-Fluoropyridin-3-yl)(4-(methylthio)phenyl)methanol

Product 1

HCID 66600001(6-Fluoropyridin-3-yl)(4-(methylthio)phenyl)methanoneYield 87.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

(6-Fluoropyridin-3-yl)(4-(methylthio)phenyl)methanol (Example 103) (1.5304 g, 6.1387 mmol) was dissolved in DCM (60 mL) and manganese(IV) oxide (Aldrich less than 5 micron, activated, 2.546 g, 29.28 mmol) was added. The reaction was stirred at room temperature for 90 minutes, and then more activated manganese (IV) oxide (2.736 g, 31.47 mmol) was added. The reaction was stirred overnight and then was filtered through a Celite® (diatomaceous earth) pad, which was washed with DCM. The filtrate was concentrated, and dried under high vacuum to give (6-fluoropyridin-3-yl)(4-(methylthio)phenyl)methanone (1.334 g). 1H NMR (CDCl3, 400 MHz) δ 8.64 (d, J=2.35 Hz, 1H), 8.26 (td, J=8.07 Hz, 2.45 Hz, 1H), 7.75 (d, J=8.61 Hz, 2H), 7.33 (d, J=8.41 Hz, 2H), 7.09 (dd, J=8.41 Hz, 2.54 Hz, 1H), 2.56 (s, 3H). m/z (ESI, pos. ion) 248 (M+H)+.

Workup

  1. stirringThe reaction was stirred overnight
  2. filtrationwas filtered through a Celite® (diatomaceous earth) pad, which
  3. washwas washed with DCM
  4. concentrationThe filtrate was concentrated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-571e460726d54815943980aa8e58d53f
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Linked notes

Loading…