Sodium hydride → HCID 62140076, compound

HRID 1477748Notes

Reaction equation

HRID 1477748 reaction equation
[H-].[Na+].[CH:3]1([OH:7])[CH2:6][CH2:5][CH2:4]1.[C:8]([C:10]1[C:11](F)=[N:12][CH:13]=[CH:14][CH:15]=1)#[N:9]>CN(C=O)C>[CH:3]1([O:7][C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:8]#[N:9])[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76218CyclobutanolHCID 27832543-Cyano-2-fluoropyridine

Product 1

HCID 62140076HCID 62140076, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH 60% dispersion in mineral oil (100 mg, 2.5 mmol) was added to a rt solution of cyclobutanol (0.13 mL, 1.6 mmol) in DMF (1.5 mL). After stirring for 1 h, 3-cyano-2-fluoropyridine (150 mg, 1.23 mmol) was added and the brown suspension was stirred at rt for 1 h. The rxn mixture was quenched with water and extracted with DCM (2×). The combined org. layers were dried (MgSO4), filtered and concentrated in vacuo to yield 2-cyclobutoxynicotinonitrile as an orange oil. LC-MS B: tR=0.76 min; [M+H]+=175.21. 1H NMR (DMSO) δH: 8.43 (m, 1H), 8.26 (dd, J1=7.6 Hz, J2=1.9 Hz, 1H), 7.17 (dd, J1=7.6 Hz, J2=5.0 Hz, 1H), 5.25 (m, 1H), 2.43 (m, 2H), 2.13 (m, 2H), 1.82 (m, 1H), 1.66 (m, 1H).

Workup

  1. stirringthe brown suspension was stirred at rt for 1 h
  2. customThe rxn mixture was quenched with water
  3. extractionextracted with DCM (2×)
  4. dry with materiallayers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15b97b90789b4211806047554905a270
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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