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

HRID 2399524Notes

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 (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 467 mg of 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-804c273ad4854570a3fd1afd4c9fdea7
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05449682

Reaction notes

Loading…