Tert-butyl 3-bromothiophene-2-carbonyl(4-methoxy-2-methylphenyl)carbamate → 8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

HRID 1853661Notes

Reaction equation

HRID 1853661 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][CH3:24])=[CH:19][C:18]=1[CH3:25])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>[CH3:24][O:23][C:20]1[CH:19]=[C:18]([CH3:25])[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

Participants

3

Reactant 1

HCID 67449069Tert-butyl 3-bromothiophene-2-carbonyl(4-methoxy-2-methylphenyl)carbamate

Product 1

HCID 674508408-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-oneYield 86.5%

Reagents, catalysts & solvents 1

HCID 178418851HCID 178418851, compoundCatalyst

Procedure

Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl(4-methoxy-2-methylphenyl)carbamate (14 g, 33 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (750 mg, 1.5 mmol) to afford the desired product (7.0 g, 85%) as a dark brown solid: ESI MS m/z 250 [C12H8FNO2S+H]+.

Sources & evidence

ORD record
ord-f1497fac37c841a0b8f3b07a73afb29e
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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