9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one → HCID 86689446, compound

HRID 1853677Notes

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].[CH2:18]([N:20]([CH:28]([C:30]1[CH:35]=[CH:34][C:33](B2OC(C)(C)C(C)(C)O2)=[CH:32][CH:31]=1)[CH3:29])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19]>>[CH2:18]([N:20]([CH:28]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=1[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])[CH3:29])[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH3:19]

Participants

Reactant 2

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

HCID 86689447HCID 86689447, compound

Product 1

HCID 86689446HCID 86689446, compoundYield 40%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (770 mg, 2.5 mmol) was reacted with tert-butyl ethyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate (1.4 g, 3.7 mmol) to afford the desired product (450 mg, 40%) as a light brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.

Sources & evidence

ORD record: ord-b4cd7a2945fc401a93bea36c4b6b5a00
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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