N-bromobutanimide → HCID 60107655, compound

HRID 853613Notes

Reaction equation

HRID 853613 reaction equation
[CH:1]1([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([O:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:16]4[C:11]([C:12]([CH3:30])=[CH:13][CH:14]=[N:15]4)=[CH:10][C:9]=3[CH2:8]2)[CH2:5][CH:4]=[CH:3][CH2:2]1.[Br:31]N1C(=O)CCC1=O>C(OCC)(=O)C>[Br:31][CH2:30][C:12]1[C:11]2[C:16](=[C:17]([O:21][C:22](=[O:29])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:18]3[C:19](=[O:20])[N:7]([CH2:6][CH:1]4[CH2:5][CH:4]=[CH:3][CH2:2]4)[CH2:8][C:9]=3[CH:10]=2)[N:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 60107657HCID 60107657, compound

Product 1

HCID 60107655HCID 60107655, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

For example, benzoic acid 7-cyclopent-3-enylmethyl-4-methyl-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-9-yl ester A17.12 is reacted with N-bromosuccinimide in refluxing ethyl acetate to afford benzoic acid 4-bromomethyl-7-cyclopent-3-enylmethyl-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-9-yl ester A17.13. This compound is heated to 120° C. with an excess of a trialkyl phosphite to give after deprotection the phenolic phosphonate ester A17.14.

Sources & evidence

ORD record
ord-df1c9161694f4c4abbb0e63d4927d54a
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

Loading…