Ethyl bromoacetate → 1,3-dihydro-2-oxo-1-(4-morpholinyl)-3-(4-pyridinyl methyl)-2H-indol-3-acetic acid, ethyl ester

HRID 22236Notes

Reaction equation

HRID 22236 reaction equation
[N:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]([CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[C:8]2=[O:23])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>>[O:23]=[C:8]1[C:9]([CH2:16][C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 233539761,3-dihydro-1-(4-morpholinyl)-3-(4-pyridinylmethyl)-2H-indol-2-one

Product 1

HCID 867476751,3-dihydro-2-oxo-1-(4-morpholinyl)-3-(4-pyridinyl methyl)-2H-indol-3-acetic acid, ethyl ester

Procedure

The product obtained from Example 20 could be reacted with sodium hydride and ethyl bromoacetate in a manner similar to Example 8 to render the product as a crystalline white solid, m.p. 168°-170° C. (hexanechloroform). High Res. Mass Spec. Calcd. for C22H25N3O4 : 396.1923 (M+H) . Found: 396. 1922.

Sources & evidence

ORD record
ord-2019bcfb4dfb4c9ba21706300e04b88c
Source dataset
uspto-grants-1995_06
Patent number
US05428035

Reaction notes

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