2,6-Difluoropyridine → HCID 67452252, compound

HRID 869173Notes

Reaction equation

HRID 869173 reaction equation
FC1C=CC([C:8]2([CH2:12][NH2:13])[CH2:11][CH2:10][CH2:9]2)=CC=1.F[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[N:16]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1(C)C=CC=CC=1>[F:21][C:17]1[N:16]=[C:15]([C:8]2([C:12]#[N:13])[CH2:11][CH2:10][CH2:9]2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 739342,6-DifluoropyridineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 24274221[1-(4-fluorophenyl)cyclobutyl]methanamine

Product 1

HCID 67452252HCID 67452252, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following the same procedure as described for 2-(3-fluoropyridin-2-yl)acetonitrile (Example 18), 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-f1e5187536184a02ba81b3b2425fa49c
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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