Water → 1-(3-Fluoropyridin-2-yl)-3-oxocyclobutane-1-carbonitrile

HRID 1474103Notes

Reaction equation

HRID 1474103 reaction equation
[F:1][C:2]1[C:3]([C:8]2([C:13]#[N:14])[CH2:11][C:10](=C)[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH2:15]>C(Cl)Cl.C(#N)C>[F:1][C:2]1[C:3]([C:8]2([C:13]#[N:14])[CH2:11][C:10](=[O:15])[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 674510301-(3-Fluoropyridin-2-yl)-3-methylenecyclobutane-1-carbonitrile

Product 1

HCID 674531411-(3-Fluoropyridin-2-yl)-3-oxocyclobutane-1-carbonitrileYield 86.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
15 °C

Procedure

To a mixture of 1-(3-fluoropyridin-2-yl)-3-methylenecyclobutanecarbonitrile (272 g, 1.45 mol) and RuCl3.H2O (9.0 g, 0.044 mol) in DCM (1 L), acetonitrile (1 L), and water (1.5 L) mixture was added solid NaIO4 (1235 g, 5.8 mol) portionwise at 10-30° C. Upon the completion of addition, the reaction was stirred 1 h at 15° C. and overnight at rt. The solid precipitate was filtered off and washed with DCM (2×1000 mL). The organic layer was washed with water (2×500 mL) and brine (500 mL), dried over Na2SO4, and concentrated to provide a crude title compound as a dark solid (238 g, 86.3%). LRMS (M+H+) m/z 191.1.

Workup

  1. additionUpon the completion of addition
  2. filtrationThe solid precipitate was filtered off
  3. washwashed with DCM (2×1000 mL)
  4. washThe organic layer was washed with water (2×500 mL) and brine (500 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9beaa3b75c0d430a89f3c92934feb93e
Source dataset
uspto-grants-2015_04
Patent number
US09018223B2

Reaction notes

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