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

HRID 1241723Notes

Reaction equation

HRID 1241723 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:16]=[CH:15][CH:14]=[CH:13][C:10]=2[CH:11]=O)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[N:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][C:30](OCC)=[O:31])=[CH:22][CH:21]=1.[Li+].CC([N-]C(C)C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3[C:10](=[CH:13][CH:14]=[CH:15][N:16]=3)[CH:11]=[C:29]([CH2:28][CH2:27][CH2:26][C:23]3[CH:22]=[CH:21][N:20]=[CH:25][CH:24]=3)[C:30]2=[O:31])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 11241221Ethyl 5-(4-pyridyl)pentanoateHCID 219366402-(4-Chloro-3-nitrophenylamino)nicotinaldehyde

Product 1

HCID 219366121-(4-chloro-3-nitrophenyl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-oneYield 34%

Procedure

The procedure of Example 1 was repeated using 2-(4-chloro-3-nitrophenylamino)nicotinaldehyde (1.0 eq.; prepared in Synthetic Example 1d)), ethyl 5-(pyridin-4-yl)pentanoate (1.5 eq.; prepared in Synthetic Example 2) and LDA (1.5 eq.) to obtain 1-(4-chloro-3-nitrophenyl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (yield 34%). The target product was purified through flash column chromatography and recrystallization, mp 136–137° C./DMF.

Sources & evidence

ORD record
ord-00b272002f284bbca184de431d4a9a0f
Source dataset
uspto-grants-2006_10
Patent number
US07115623B2

Reaction notes

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