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

HRID 478744Notes

Reaction equation

HRID 478744 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH:13]=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH2:26][CH2:27][CH2:28][C:29](OCC)=[O:30])[CH:20]=1.[Li+].CC([N-]C(C)C)C>CN(C=O)C.CCO>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:11]3[C:12](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:28]([CH2:27][CH2:26][CH2:25][C:21]3[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=3)[C:29]2=[O:30])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 121149522-(3-Nitro-phenylamino)-pyridine-3-carbaldehydeHCID 12904538Ethyl 5-(pyridin-3-yl)pentanoate

Product 1

HCID 120746221-(3-nitrophenyl)-3-[3-(pyridin-3-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-(3-nitrophenylamino)nicotinaldehyde (1.0 eq.), ethyl 5-(pyridin-3-yl)pentanoate (1.1 eq., prepared in Synthetic Example 9) and LDA (1.5 eq.) to obtain 1-(3-nitrophenyl)-3-[3-(pyridin-3-yl)propyl]-1,8-naphthyridin-2(1H)-one, mp 172 to 173° C./DMF-EtOH. 1H NMR(CDCl3) δ: 2.02-2.11(2H, m), 2.71-2.79 (4H, m), 7.18-7.24 (2H, m), 7.54-7.92(5H, m), 8.19-8.20 (1H, m), 8.34-8.49(4H, m).

Sources & evidence

ORD record
ord-28d525cc6d9640bfac052acaada011b8
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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