Tert-butyl 3-bromothiophene-2-carbonyl(2-fluoro-4-methoxyphenyl)carbamate → 6-Fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one

HRID 1853655Notes

Reaction equation

HRID 1853655 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[F: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>[F:25][C:18]1[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]=[C:20]([O:23][CH3:24])[CH:19]=1

Participants

3

Reactant 1

HCID 67450251Tert-butyl 3-bromothiophene-2-carbonyl(2-fluoro-4-methoxyphenyl)carbamate

Product 1

HCID 674472746-Fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-oneYield 82.9%

Reagents, catalysts & solvents 1

HCID 178418851HCID 178418851, compoundCatalyst

Procedure

Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl(2-fluoro-4-methoxyphenyl)carbamate (2.0 g, 4.6 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (100 mg, 0.20 mmol) to afford the desired product (950 mg, 80%) as a dark brown solid: ESI MS m/z 250 [C12H8FNO2S+H]+.

Sources & evidence

ORD record
ord-849f9b87cacf41e594efe4d49a863e59
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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