N-bromobutanimide → 9-Bromo-8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one

HRID 1853650Notes

Reaction equation

HRID 1853650 reaction equation
[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[NH:15][C:14](=[O:19])[C:13]3[S:20][CH:21]=[CH:22][C:12]=3[C:11]=2[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:23]N1C(=O)CCC1=O>>[Br:23][C:10]1[C:11]2[C:12]3[CH:22]=[CH:21][S:20][C:13]=3[C:14](=[O:19])[NH:15][C:16]=2[CH:17]=[CH:18][C:9]=1[O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 674475778-(tert-Butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 674481399-Bromo-8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-oneYield 37.7%

Procedure

Following Step 4 from General Procedure A, 8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one (740 mg, 2.2 mmol) was reacted with N-bromosuccinimide (480 mg, 2.7 mmol) to afford the desired product (340 mg, 37%) as a brown solid: ESI MS m/z 411 [C17H20BrNO2SSi+H]+.

Sources & evidence

ORD record
ord-d11a93154d754729adfa577f7bdf7d62
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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