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

HRID 478748Notes

Reaction equation

HRID 478748 reaction equation
[N+](C1C=C(N[C:11]2[N:18]=[CH:17][CH:16]=[CH:15][C:12]=2C=O)C=CC=1)([O-])=O.C[C:20]1[N:29]=[C:28]2[C:23]([CH:24]=[C:25]([CH2:40][CH2:41][CH2:42]C3C=CN=CC=3)[C:26](=[O:39])[N:27]2[C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([N+:36]([O-:38])=[O:37])[CH:31]=2)=[CH:22][CH:21]=1.[Li+].[CH3:50]C([N-]C(C)C)C>CN(C=O)C>[N+:36]([C:32]1[CH:31]=[C:30]([N:27]2[C:28]3[C:23](=[CH:22][CH:21]=[CH:20][N:29]=3)[CH:24]=[C:25]([CH2:40][CH2:41][CH2:42][CH2:50][C:11]3[CH:12]=[CH:15][CH:16]=[CH:17][N:18]=3)[C:26]2=[O:39])[CH:35]=[CH:34][CH:33]=1)([O-:38])=[O:37]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 121149522-(3-Nitro-phenylamino)-pyridine-3-carbaldehydeHCID 180026127-methyl-1-(3-nitrophenyl)-3-[3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one

Product 1

HCID 120746241-(3-nitrophenyl)-3-[4-(pyridin-2-yl)butyl]-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure of Example 1 was repeated using 2-(3-nitrophenylamino)nicotinaldehyde (1.0 eq.), ethyl 6-(pyridin-2-yl)hexanoate (2.0 eq., prepared in Synthetic Example 11) and LDA (2.0 eq.) to obtain 1-(3-nitrophenyl)-3-[4-(pyridin-2-yl)butyl]-1,8-naphthyridin-2(1H)-one, mp 163 to 165° C./DMF, wherein the product was purified through silica gel column chromatography and recrystallization.

Sources & evidence

ORD record
ord-7686cef401a342e9a0feb9b2245a939b
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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