N-bromobutanimide → 9-Bromo-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one

HRID 1853656Notes

Reaction equation

[F:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[C:8]3[S:13][CH:14]=[CH:15][C:7]=3[C:6]=2[CH:5]=[C:4]([O:16][CH3:17])[CH:3]=1.[Br:18]N1C(=O)CCC1=O>>[Br:18][C:5]1[C:6]2[C:7]3[CH:15]=[CH:14][S:13][C:8]=3[C:9](=[O:12])[NH:10][C:11]=2[C:2]([F:1])=[CH:3][C:4]=1[O:16][CH3:17]

Participants

Reactant 2

HCID 67184N-bromobutanimide

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

Product 1

HCID 674487569-Bromo-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-oneYield 61%

Procedure

Following Step 4 from General Procedure A, 6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.0 g, 4.0 mmol) was reacted with N-bromosuccinimide (570 mg, 4.8 mmol) to afford the desired product (800 mg, 61%) as a brown solid: ESI MS m/z 329 [C12H7BrFNO2S+H]+.

Sources & evidence

ORD record: ord-072306e68eb844e7964088d4b783f0e0
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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