Lithium diisopropylamide → HCID 18002630, compound

HRID 478755Notes

Reaction equation

HRID 478755 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].[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[CH2:24][CH2:25][CH2:26][CH2:27][C:28](OCC)=[O:29].[Li+].CC([N-]C(C)C)C>CN(C=O)C>[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:27]([CH2:26][CH2:25][CH2:24][C:20]3[O:19][CH:23]=[CH:22][CH:21]=3)[C:28]2=[O:29])[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 12594355Ethyl 5-(furan-2-yl)pentanoate

Product 1

HCID 18002630HCID 18002630, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure of Example 1 was repeated using 2-(3-nitrophenylamino)nicotinaldehyde (1.0 eq.), ethyl 5-(2-furyl)pentanoate (1.5 eq., prepared in Synthetic Example 18) and LDA (1.5 eq.) to obtain 1-(3-nitrophenyl)-3-[3-(2-furyl)propyl]-1,8-naphthyridin-2(1H)-one, mp 166 to 167° C./DMF, wherein the product was purified through silica gel column chromatography and recrystallization.

Sources & evidence

ORD record
ord-8997bca527f44a59a7cdaa508d0e1d15
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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