N-(2-bromo-4-methoxyphenyl)-5-methyl-N-(5-methylthiophene-2-carbonyl)thiophene-2-carboxamide → 8-Methoxy-2-methylthieno[2,3-c]quinolin-4(5H)-one

HRID 1853652Notes

Reaction equation

HRID 1853652 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]([C:19]([C:21]1[S:22][C:23]([CH3:26])=[CH:24][CH:25]=1)=[O:20])C(C1SC(C)=CC=1)=O>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>[CH3:9][O:8][C:6]1[CH:7]=[CH:2][C:3]2[NH:10][C:19](=[O:20])[C:21]3[S:22][C:23]([CH3:26])=[CH:24][C:25]=3[C:4]=2[CH:5]=1

Participants

3

Reactant 1

HCID 67447412N-(2-bromo-4-methoxyphenyl)-5-methyl-N-(5-methylthiophene-2-carbonyl)thiophene-2-carboxamide

Product 1

HCID 674475738-Methoxy-2-methylthieno[2,3-c]quinolin-4(5H)-oneYield 481.8%

Reagents, catalysts & solvents 1

HCID 178418851HCID 178418851, compoundCatalyst

Procedure

Following Step 3 from General Procedure A, N-(2-bromo-4-methoxyphenyl)-5-methyl-N-(5-methylthiophene-2-carbonyl)thiophene-2-carboxamide (500 mg, 1.1 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (45 mg, 0.089 mmol) to afford the desired product (1.3 g, 48%) as a green solid: ESI MS m/z 246 [C13H11NO2S+H]+.

Sources & evidence

ORD record
ord-c4f8232274154e2a8a24dae87cdf7ee4
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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