Cyanide → 3-Bromopyridine-2-carbonitrile

HRID 423177Notes

Reaction equation

HRID 423177 reaction equation
[Br:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.[C-:9]#[N:10]>N1C=CC=CC=1>[Br:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5975CyanideHCID 142763Pyridine, 3-bromo-, 1-oxide

Product 1

HCID 8176943-Bromopyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In Scheme I is described the preparation of pyridine intermediates (5) and (6). In Scheme I, Step 1,3-bromopyridine (1) is oxidized to 3-bromo-pyridine-N-oxide (2). In Scheme I, Step 2, cyanide addition gives 3-bromo-pyridine-2-carbonitrile (3). The nitrile of formula (3) is hydrolyzed to the carboxylic acid and esterified with acid catalysis to the ester of formula (4). In Scheme I, Step 4, the ester is reduced to the pyridylmethanol of formula (5a) using sodium borohydride.

Sources & evidence

ORD record
ord-0d6d80b5e8f347ff8cbffc974dbc79d0
Source dataset
uspto-grants-2012_01
Patent number
US08101761B2

Reaction notes

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