Lithium diisopropylamide → 1-(3-cyanophenyl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one

HRID 478759Notes

Reaction equation

HRID 478759 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[N:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][C:28](OCC)=[O:29])=[CH:20][CH:19]=1.[Li+].CC([N-]C(C)C)C>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:10]3[C:11](=[CH:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:27]([CH2:26][CH2:25][CH2:24][C:21]3[CH:20]=[CH:19][N:18]=[CH:23][CH:22]=3)[C:28]2=[O:29])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 11241221Ethyl 5-(4-pyridyl)pentanoateHCID 139581262-(3-Cyanophenylamino)nicotinaldehyde

Product 1

HCID 180026491-(3-cyanophenyl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure of Example 1 was repeated using 2-(3-cyanophenylamino)nicotinaldehyde (1.0 eq.), ethyl 5-(4-pyridyl)pentanoate (1.2 eq., prepared in Synthetic Example 10) and LDA (1.2 eq.) to obtain 1-(3-cyanophenyl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one, mp 202 to 203.5° C./DMF.

Sources & evidence

ORD record
ord-103032c6d9924014bbe5825ff0f09dc3
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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