tert-Butyl 3-Bromothiophene-2-carbonyl[4-(tert-butyldimethylsilyloxy)phenyl]carbamate → 8-(tert-Butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one

HRID 1853649Notes

Reaction equation

HRID 1853649 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([N:9]([C:17]1[CH:22]=[CH:21][C:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])=[CH:19][CH:18]=1)C(=O)OC(C)(C)C)=[O:8]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Si:24]([O:23][C:20]1[CH:19]=[CH:18][C:17]2[NH:9][C:7](=[O:8])[C:3]3[S:4][CH:5]=[CH:6][C:2]=3[C:22]=2[CH:21]=1)([C:27]([CH3:29])([CH3:30])[CH3:28])([CH3:26])[CH3:25]

Participants

3

Reactant 1

HCID 86689440tert-Butyl 3-Bromothiophene-2-carbonyl[4-(tert-butyldimethylsilyloxy)phenyl]carbamate

Product 1

HCID 674475778-(tert-Butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-oneYield 111.6%

Reagents, catalysts & solvents 1

HCID 178418851HCID 178418851, compoundCatalyst

Procedure

Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl[4-(tert-butyldimethylsilyloxy)phenyl]carbamate (1.0 g, 2.0 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (50 mg, 0.098 mmol) to afford the desired product (740 mg, quant.) as a solid: ESI MS m/z 332 [C17H21NO2SSi+H]+.

Sources & evidence

ORD record
ord-60eab21d366149db84190de6a35a27a4
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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