Water ethanol → HCID 68412965, compound

HRID 1942267Notes

Reaction equation

HRID 1942267 reaction equation
[F:1][C:2]1[C:3]([N:8]2[CH2:13][CH:12]=[C:11]([C:14]#[N:15])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C([OH:18])C.O>>[F:1][C:2]1[C:3]([N:8]2[CH2:9][CH:10]=[C:11]([C:14]([NH2:15])=[O:18])[CH2:12][CH2:13]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 19096565Water ethanolHCID 59334802HCID 59334802, compound

Product 1

HCID 68412965HCID 68412965, compoundYield 100%

Procedure

3′-Fluoro-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carbonitrile 20 (10.0 g, 49.2 mMol) was dissolved in ethanol:water (2:1, 150 mL) with stirring and heating. PtH(PMe2O)2(PMe2OH) (50 mg, 0.025 mol %) was added and the solution stirred under reflux for 2 h. LC/MS showed the reaction to be 100% complete after this time. The cooled solution was evaporated to dryness in vacuo to leave a white solid. The solid was filtered through a flash pad of silica gel to remove the catalyst to give the title compound as a white solid (10.9 g, 100%).

Workup

  1. temperatureheating
  2. stirringthe solution stirred
  3. temperatureunder reflux for 2 h
  4. customthe reaction
  5. customThe cooled solution was evaporated to dryness in vacuo
  6. customto leave a white solid
  7. filtrationThe solid was filtered through a flash pad of silica gel
  8. customto remove the catalyst

Sources & evidence

ORD record
ord-5194f43549e94132b2e0386ea13c2e48
Source dataset
uspto-grants-2013_03
Patent number
US08389549B2

Reaction notes

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