Sodium Cyanide → 5-Bromo-4-methylpyridine-2-carbonitrile

HRID 1047229

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][N:3]=1.[Cu](C#N)[C:11]#[N:12].[C-]#N.[Na+]>CN(C)C=O>[Br:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:11]#[N:12])=[N:3][CH:4]=1

Participants

Conditions

Temperature: 158 °C

Procedure

2,5-Dibromo-4-methylpyridine (5.0 g, 19.9 mmol), copper cyanide (1.43 g, 15.9 mmol), sodium cyanide (0.801 g, 16.3 mmol) and dimethylformamide (30 mL) were combined in a sealed reaction vessel and heated at 158° C. for 3 h. The reaction mixture was purified by silica gel column chromatography (0-80% ethyl acetate in hexanes). The resulting material was subjected to a second silica gel column (0-20% methanol in dichloromethane). Clean fractions were combined and concentrated to afford the title compound as a white solid (2.30 g, 11.6 mmol, 58% yield). MS (ESI) m/z 198.0 [M+1]+.

Workup

customThe reaction mixture was purified by silica gel column chromatography (0-80% ethyl acetate in hexanes)
concentrationconcentrated

Sources & evidence

ORD record: ord-7189f46228d94371aad57718a868976f
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569494B2

Linked notes

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