9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one → HCID 86689458, compound

HRID 1853692Notes

Reaction equation

HRID 1853692 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].[CH:18]1([CH:23]([C:33]2[CH:38]=[CH:37][C:36](B3OC(C)(C)C(C)(C)O3)=[CH:35][CH:34]=2)[CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:22][CH2:21][CH2:20][CH2:19]1>>[CH:18]1([CH:23]([C:33]2[CH:38]=[CH:37][C:36]([C:2]3[C:3]4[C:4]5[CH:17]=[CH:16][S:15][C:5]=5[C:6](=[O:14])[NH:7][C:8]=4[CH:9]=[CH:10][C:11]=3[O:12][CH3:13])=[CH:35][CH:34]=2)[CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-oneHCID 86689459HCID 86689459, compound

Product 1

HCID 86689458HCID 86689458, compoundYield 19%

Procedure

Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one) (500 mg, 1.6 mmol) was reacted with tert-butyl 2-cyclopentyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamate (1.3 g, 3.2 mmol) to afford the desired product (150 mg, 19%) as a yellow solid: ESI MS m/z 519 [C30H34N2O4S+H]+.

Sources & evidence

ORD record
ord-37a53cb1260b48d0b8652ab0d7306c42
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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