Dimethylformamide → HCID 19012291, compound
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])=[CH:5][CH:4]=1.[CH3:17][N:18]([CH:20]=[O:21])C>>[CH2:5]([C:17]1[N:18]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]#[N:16])=[CH:5][CH:4]=2)[C:20](=[O:21])[CH:2]=[CH:3][CH:4]=1)[CH2:6][CH2:7][CH3:8]Participants
Procedure
1.12 g of potassium tert-butylate are added to a solution of 1.5 g of 6-butyl-1,2-dihydro-2-oxopyridine ["IIIa"; m.p. 69°; obtainable by condensation of hexan-2-one with ethyl formate in toluene, in the presence of NaOCH3, to give 1-hydroxyhept-1-en-3-one, condensation with cyanoacetamide in water, in the presence of piperidine and acetic acid, at 90°, to give 6-butyl-3-cyano-1,2-dihydro-2-oxopyridine ("IIIb"; m.p. 110°), hydrolysis with 37% hydrochloric acid (boiling for 5 hours) to give 6-butyl-1,2-dihydro-2-oxopyridine-3-carboxylic acid (m.p. 149°) and decarboxylation at 180°-200°] in 25 ml of DMF. The mixture is stirred for 10 minutes, a solution of 2.72 g of 4'-bromomethyl-2-cyanobiphenyl ("IIa") in 15 ml of DMF is added dropwise over 30 minutes and the resulting mixture is stirred for 16 hours at 20°. It is evaporated, worked up in a conventional manner (pH 7; ethyl acetate) and purified by chromatography (silica gel; methylene chloride/methanol 98:2) to give 6-butyl-1-(2'-cyanobiphenyl-4-ylmethyl)-1,2-dihydro-2-oxopyridine; Rf 0.4; (M+H)+ 343. 6-Butyl-2-(2'-cyanobiphenyl-4-yl-methoxy)pyridine is obtained as a by-product.
Workup
- stirringthe resulting mixture is stirred for 16 hours at 20°
- customIt is evaporated
- custompurified by chromatography (silica gel; methylene chloride/methanol 98:2)
Sources & evidence
- ORD record
- ord-cbab6b5f683843a8823f6b13bd6facc0
- Source dataset
- uspto-grants-1994_07
- Patent number
- US05332750
Reaction notes
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