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

HRID 478758Notes

Reaction equation

HRID 478758 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2[N:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=O)[CH:2]=1.[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][C:26](OCC)=[O:27])=[CH:18][CH:17]=1.[Li+].CC([N-]C(C)C)C>CN(C=O)C.CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:8]3[C:9](=[CH:12][CH:13]=[CH:14][N:15]=3)[CH:10]=[C:25]([CH2:24][CH2:23][CH2:22][C:19]3[CH:18]=[CH:17][N:16]=[CH:21][CH:20]=3)[C:26]2=[O:27])[CH:2]=1

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 11241221Ethyl 5-(4-pyridyl)pentanoateHCID 180026102-(Pyridin-3-ylamino)nicotinaldehyde

Product 1

HCID 101321621-(pyridin-3-yl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 19794673N,N-dimethylformamide ethanolSolvent

Procedure

The procedure of Example 1 was repeated using 2-(pyridin-3-ylamino)nicotinaldehyde (1.0 eq., prepared in Synthetic Example 3), ethyl 5-(pyridin-4-yl)pentanoate (1.5 eq., prepared in Synthetic Example 10) and LDA (1.5 eq.) to obtain 1-(pyridin-3-yl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one, mp 178 to 180° C./DMF-EtOH.

Sources & evidence

ORD record
ord-67cc190c20e943a786bbb86747e06fe6
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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