Sodium hydride → HCID 86744250, compound

HRID 1087785Notes

Reaction equation

[CH3:1][CH:2]([CH3:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[H-].[Na+].Cl[CH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[N:16]1[C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[N:28][C:29]([Cl:35])=[CH:30][CH:31]=2)[N:26]=1>>[Cl:35][C:29]1[N:28]=[C:27]2[C:32]([CH:33]=[CH:34][C:25]([N:16]3[C:17](=[O:24])[C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:15]3[CH:4]([C:3](=[O:10])[CH:2]([CH3:1])[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N:26]2)=[CH:31][CH:30]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 81583Ethyl isobutyrylacetate

HCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 86744250HCID 86744250, compoundYield 77.5%

Procedure

Ethyl 2-[2-(7-chloro-1,8-naphthyridin-2-yl)-4-methyl-3-oxopentanoate may be prepared by working in a manner similar to that described in Example 23, but starting with ethyl 4-methyl-3-oxopentanoate (4.7 g), an oily suspension (50% by weight; 1.2 g) of sodium hydride and 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (6.6 g). After recrystallization in diisopropyl ether, ethyl 2-[2-(7-chloro-1, 8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl]-4-methyl-3-oxopentanoate (7 g), m.p. 146° C., is thereby obtained.

Workup

customAfter recrystallization in diisopropyl ether

Sources & evidence

ORD record: ord-f5bbe4e54fd2494aa05a5f6739de86fe
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04960779

Reaction notes

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