1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one → 4-Acetylphenyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one

HRID 1853781Notes

Reaction equation

HRID 1853781 reaction equation
Br[C:2]1[C:3]2[C:4]3[CH:17]=[CH:16][S:15][C:5]=3[C:6](=[O:14])[NH:7][C:8]=2[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].CC1(C)C(C)(C)OB([C:26]2[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][CH:27]=2)O1>>[C:32]([C:29]1[CH:30]=[CH:31][C:26]([C:17]2[C:4]3[C:3]4[CH:2]=[C:11]([O:12][CH3:13])[CH:10]=[CH:9][C:8]=4[NH:7][C:6](=[O:14])[C:5]=3[S:15][CH:16]=2)=[CH:27][CH:28]=1)(=[O:34])[CH3:33]

Participants

3

Reactant 2

HCID 27605961-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-oneHCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 866894914-Acetylphenyl-8-methoxythieno[2,3-c]quinolin-4(5H)-oneYield 46.5%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.0 g, 3.2 mmol) was reacted with 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone (1.2 g, 4.8 mmol) to afford the desired product (520 mg, 46%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 8.16 (d, J=8.1 Hz, 2H), 7.61-7.54 (m, 2H), 7.45-7.39 (m, 3H), 6.05 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 2.71 (s, 3H).

Sources & evidence

ORD record
ord-58fc3c061f6b4b07bcdf92b9d837ede8
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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