tert-butyl N-(1-(4-bromophenyl)ethyl)carbamate → tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

HRID 1853812Notes

Reaction equation

HRID 1853812 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.Br[C:19]1[C:20]2[C:21]3[CH:34]=[CH:33][S:32][C:22]=3[C:23](=[O:31])[NH:24][C:25]=2[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]>>[CH3:30][O:29][C:28]1[CH:27]=[CH:26][C:25]2[NH:24][C:23](=[O:31])[C:22]3[S:32][CH:33]=[CH:34][C:21]=3[C:20]=2[C:19]=1[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 11983730tert-butyl N-(1-(4-bromophenyl)ethyl)carbamateHCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 67458078tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamateYield 50%

Procedure

Following General Procedure E, tert-butyl 1-(4-bromophenyl)ethylcarbamate (3.0 g, 10 mmol) was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.8 g, 9.0 mmol) to afford the desired product (2.0 g, 50%) as a brown solid: ESI MS m/z 451 [C25H26N2O4S+H]+.

Sources & evidence

ORD record
ord-357e2d5f47aa476c92ea38022b698a32
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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