Hydrochloric Acid → 3-(5-Cyano-3'-trifluoromethyl-[2,2']bipyridinyl-6-yl)-2-oxo-propionic acid ethyl ester

HRID 2113631Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]#[N:19].[C:20](OCC)(=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].Cl>CCO.CC[O-].[Na+]>[CH2:24]([O:23][C:21](=[O:22])[C:20](=[O:26])[CH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]#[N:19])[CH3:25]

Participants

Conditions

Temperature: 50 °C

Procedure

Dissolve 6-methyl-3′-trifluoromethyl-[2,2′]bipyridinyl-5-carbonitrile (150 mg, 0.570 mmol) and diethyl oxalate (150 mg, 1.03 mmol) in a solution of EtOH (2 mL) and 17% NaOEt in EtOH (0.6 mL, 1.71 mmol). Warm the mixture to 50° C. and stir overnight. Pour the mixture onto ice water (50 mL) and acidify with 3 N HCl. Extract with EtOAc (3×50 mL). Dry the combined organic extracts over Na2SO4 and remove the solvent under reduced pressure. Purify the crude product using silica gel chromatography eluting with EtOAc/hexane (1:1) to yield the title compound. MS 364.11 (M+1).

Workup

additionPour the mixture onto ice water (50 mL)
extractionExtract with EtOAc (3×50 mL)
dry with materialDry the combined organic extracts over Na2SO4
customremove the solvent under reduced pressure
customPurify the crude product
washeluting with EtOAc/hexane (1:1)

Sources & evidence

ORD record: ord-33846280075b475f839875b92d3a4dfe
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432275B2

Reaction notes

Loading…