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

HRID 653642Notes

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 620 mg (1.8 mmol) of the product of Step D and CuCN (806 mg, 9.0 mmol) was heated in pyridine (4 mL) at reflux for 10 hours under nitrogen. The reaction was cooled, then water (50mL), KCN (1.17g), 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 the title compound as a tan solid.

Workup

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

Sources & evidence

ORD record: ord-07cf56ad76b648528d9473aecc08beae
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05128327

Reaction notes

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