N-bromobutanimide → HCID 86689498, compound

HRID 1853815Notes

Reaction equation

HRID 1853815 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:31]=[CH:30][C:20]([CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:19][CH:18]=1.[Br:32]N1C(=O)CCC1=O>CN(C=O)C>[Br:32][C:11]1[C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]([C:17]2[CH:31]=[CH:30][C:20]([CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[CH:19][CH:18]=2)=[C:3]([O:2][CH3:1])[CH:12]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67447234HCID 67447234, compound

Product 1

HCID 86689498HCID 86689498, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following General Procedure I, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (0.66 g, 1.5 mmol) was reacted with N-bromosuccinimide (0.30 g, 1.7 mmol) in DMF (10 mL) to afford the desired product (0.39 g, 51%) as a brown solid: ESI MS m/z 515 [C24H23BrN2O4S+H]+.

Sources & evidence

ORD record
ord-bdd6f5f964394af69a428bcece3fa176
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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