N-bromobutanimide → Tert-butyl (1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate

HRID 1853848Notes

Reaction equation

HRID 1853848 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:22]=[CH:21][C:20]([C:23]2([CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:25][CH2:24]2)=[CH:19][CH:18]=1.C1C(=O)N([Br:42])C(=O)C1>>[Br:42][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:22]=[CH:21][C:20]([C:23]3([CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:33])[CH3:32])[CH2:24][CH2:25]3)=[CH:19][CH:18]=2)=[C:3]([O:2][CH3:1])[CH:12]=1

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 68229068Tert-butyl (1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate

Product 1

HCID 86689527Tert-butyl (1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamateYield 54.2%

Procedure

Following General Procedure I, tert-butyl (1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate (750 mg, 1.57 mmol) was reacted with NBS (280 mg, 1.57 mmol)) to afford the desired product (473 mg, 54%) as a yellow solid: ESI MS m/z 555 [C27H27BrN2O4S+H]+.

Sources & evidence

ORD record
ord-60925a73ad1140aca2766641e2330f0e
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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