Triethylamine → 2-Cyano-3-fluoropyridine

HRID 1441857Notes

Reaction equation

HRID 1441857 reaction equation
[F:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.C[Si]([C:13]#[N:14])(C)C.C(N(CC)CC)C>C(#N)C>[C:13]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 123084Pyridine, 3-fluoro-, 1-oxide

Product 1

HCID 70604082-Cyano-3-fluoropyridineYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Fluoropyridine-1-oxide (10.0 g, 88.4 mmol), trimethylsilylcyanide (26.32 g, 265.3 mmol), and triethylamine (17.89 g, 177 mmol) were reacted in 90 mL of acetonitrile utilizing the procedure described in example 762B. Purification of the crude by silica gel chomatography using CH2Cl2 as eluent gives compound 771B (7.5 g, 70%) as a light yellow solid.

Workup

  1. customPurification of the crude by silica gel chomatography

Sources & evidence

ORD record
ord-c3787faca39d4d86bb97588eb3da68fd
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Reaction notes

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