Water → 3-Benzyl-5-cyano-2-ethyl-7-methylimidazo[4,5-b]pyridine

HRID 36101Notes

Reaction equation

[CH2:1]([N:8]1[C:12]2=[N:13][C:14](Br)=[CH:15][C:16]([CH3:17])=[C:11]2[N:10]=[C:9]1[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([Cu])#[N:22].O.[C-]#N.[K+]>N1C=CC=CC=1.CCOC(C)=O>[CH2:1]([N:8]1[C:12]2=[N:13][C:14]([C:21]#[N:22])=[CH:15][C:16]([CH3:17])=[C:11]2[N:10]=[C:9]1[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-benzyl-5-bromo-2-ethyl-7-methylimidazo[4,5-b]pyridine (0.62 g, 1.8 mmol) and CuCN (0.806 g, 9.0 mmol) was heated in pyridine (4 mL) at reflux for 10 h under nitrogen. The reaction was cooled, then water (50 mL), KCN (1.17 g), and EtOAc (20 mL) were added and the mixture was heated to 50° C. for 5 min. Cooling and extraction with EtOAc (2×50 mL) gave 3-benzyl-5-cyano-2-ethyl-7-methylimidazo[4,5-b]pyridine as a tan solid.

Workup

temperatureat reflux for 10 h under nitrogen
temperatureThe reaction was cooled
temperatureCooling
extractionextraction with EtOAc (2×50 mL)

Sources & evidence

ORD record: ord-2e74cfb894b449a7bdb6636d393adc37
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05412097

Reaction notes

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