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

HRID 1621582

반응식

HRID 1621582 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매2회HCID 6344Dichloromethane용매

실험 절차

(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 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)+.

후처리

  1. addition2.546 g, 29.28 mmol) was added
  2. stirringThe reaction was stirred overnight
  3. filtrationwas filtered through a Celite® (diatomaceous earth) pad, which
  4. washwas washed with DCM
  5. concentrationThe filtrate was concentrated
  6. customdried under high vacuum

출처 및 근거

ORD 기록
ord-80141495bbd847db93a4ea4c7d02c15e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772480B2

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