Lithium diisopropylamide → HCID 9843930, compound

HRID 1241717Notes

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].[CH3:19][CH:20]([C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][C:24](OCC)=[O:25].[Li+].CC([N-]C(C)C)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:23]([CH2:22][CH2:21][CH:20]([CH3:19])[C:29]3[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=3)[C:24]2=[O:25])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Reactant 3

HCID 2724682Lithium diisopropylamide

HCID 121149522-(3-Nitro-phenylamino)-pyridine-3-carbaldehyde

HCID 21936633HCID 21936633, compound

Product 1

HCID 9843930HCID 9843930, compoundYield 37%

Procedure

The procedure of Example 1 was repeated using 2-(3-nitrophenylamino)nicotinaldehyde (1.0 eq.), ethyl 5-methyl-5-(pyridin-4-yl)pentanoate (1.5 eq.; prepared in Synthetic Example 8) and LDA(1.5 eq.) to obtain 1-(3-nitrophenyl)-3-[3-methyl-3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (yield, 37%). The product was purified through flash column chromatography and recrystallization (mp 154–155° C./DMF).

Sources & evidence

ORD record: ord-8be01486a6564a73b2ec5cc5139026c2
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115623B2

Reaction notes

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