Triethylamine → 2-Cyano-3-fluoropyridine

HRID 2110479Notes

Reaction equation

HRID 2110479 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-38153988b4834f60a14a6cbb6a0f3e9b
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

Loading…