9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one → HCID 86689450, compound

HRID 1853681Notes

Reaction equation

HRID 1853681 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].[CH3:18][CH:19]([CH3:45])[CH:20]([C:30]1[CH:35]=[CH:34][C:33](B2OC(C)(C)C(C)(C)O2)=[CH:32][CH:31]=1)[CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:8]2[NH:7][C:6](=[O:14])[C:5]3[S:15][CH:16]=[CH:17][C:4]=3[C:3]=2[C:2]=1[C:33]1[CH:32]=[CH:31][C:30]([CH:20]([CH:19]([CH3:45])[CH3:18])[CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-oneHCID 86689451HCID 86689451, compound

Product 1

HCID 86689450HCID 86689450, compoundYield 20%

Procedure

Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one) (800 mg, 2.58 mmol) was reacted with tert-butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (1.2 g, 3.09 mmol) to afford the desired product (250 mg, 20%) as a yellow solid: ESI MS m % z 493 [C28H32N2O4S+H]+.

Sources & evidence

ORD record
ord-c19ccc214e67499db22912e4ffe5fb98
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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