Triethylamine → 2-Cyano-3-fluoropyridine

HRID 2378461Notes

Reaction equation

HRID 2378461 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 chromatography 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 chromatography

Sources & evidence

ORD record
ord-aa066da32d204fabb63d1b71b19c95b1
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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