2,6-Difluoropyridine → HCID 67452252, compound

HRID 1853108Notes

Reaction equation

HRID 1853108 reaction equation
F[C:2]1[C:3](CC#N)=[N:4][CH:5]=[CH:6][CH:7]=1.F[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[N:13]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1(C)C=CC=CC=1>[F:18][C:14]1[N:13]=[C:12]([C:2]2([C:3]#[N:4])[CH2:7][CH2:6][CH2:5]2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 739342,6-DifluoropyridineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 19703484(3-Fluoropyridin-2-yl)acetonitrile

Product 1

HCID 67452252HCID 67452252, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following the same procedure as above for 2-(3-fluoropyridin-2-yl)acetonitrile with 2,6-difluoropyridine (5.0 g, 43 mmol, 1.0 equiv), cyclobutylcarbonitrile (3.5 g, 43 mmol, 1.0 equiv) and NaHMDS (2.0 M in THF, 24 mL, 47 mmol, 1.1 equiv) in toluene (100 mL) gave the desired product (4.9 g, 64%) as a colorless oil following purification over silica gel using 25% EtOAc/hexanes as eluent.

Sources & evidence

ORD record
ord-ffb953f24efd4e1880be4cf7b386d0a1
Source dataset
uspto-grants-2015_02
Patent number
US08962632B2

Reaction notes

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