9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one → HCID 67447734, compound

HRID 1853678Notes

Reaction equation

HRID 1853678 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][N:19]([CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][CH:30]=1)[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23]>>[C:22]([O:21][C:20](=[O:26])[N:19]([CH2:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32]([C:2]2[C:3]3[C:4]4[CH:17]=[CH:16][S:15][C:5]=4[C:6](=[O:14])[NH:7][C:8]=3[CH:9]=[CH:10][C:11]=2[O:12][CH3:13])=[CH:33][CH:34]=1)[CH3:18])([CH3:25])([CH3:23])[CH3:24]

Participants

3

Reactant 2

HCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-oneHCID 896760711,1-Dimethylethyl N-methyl-N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate

Product 1

HCID 67447734HCID 67447734, compoundYield 59.5%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.4 g, 7.6 mmol) was reacted with tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl)carbamate (4.2 g, 11 mmol) to afford the desired product (2.1 g, 40%) as a light brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.

Sources & evidence

ORD record
ord-31633b0bc7564fa9a998f6bea04ad88b
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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