Lithium diisopropylamide → 7-methyl-1-(3-methylthiophenyl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one

HRID 478747Notes

Reaction equation

HRID 478747 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17][CH3:18])[CH:12]=2)[N:3]=1.[N:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][C:29](OCC)=[O:30])=[CH:21][CH:20]=1.[Li+].CC([N-]C(C)C)C>CCOC(C)=O>[CH3:1][C:2]1[N:3]=[C:4]2[C:5]([CH:6]=[C:28]([CH2:27][CH2:26][CH2:25][C:22]3[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=3)[C:29](=[O:30])[N:10]2[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17][CH3:18])[CH:12]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 11241221Ethyl 5-(4-pyridyl)pentanoateHCID 880211416-Methyl-2-(3-methylthiophenylamino)nicotinaldehyde

Product 1

HCID 120746237-methyl-1-(3-methylthiophenyl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The procedure of Example 1 was repeated using 6-methyl-2-(3-methylthiophenylamino)nicotinaldehyde (1.0 eq., prepared in Synthetic Example 2), ethyl 5-(pyridin-4-yl)pentanoate (1.5 eq.) and LDA (1.5 eq.) to obtain 7-methyl-1-(3-methylthiophenyl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one, mp 158 to 159° C./AcOEt, wherein the product was purified through silica gel column chromatography and recrystallization.

Sources & evidence

ORD record
ord-4b96177773ce49008d2e9e0ba086cf5c
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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