9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one → Tert-butyl (1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate

HRID 1853664Notes

Reaction equation

HRID 1853664 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].[C:18]([O:22][C:23](=[O:44])[NH:24][CH2:25][C:26]1([C:29]2[CH:34]=[CH:33][C:32](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:30]=2)[CH2:28][CH2:27]1)([CH3:21])([CH3:20])[CH3:19]>>[C:18]([O:22][C:23](=[O:44])[NH:24][CH2:25][C:26]1([C:29]2[CH:30]=[CH:31][C:32]([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:33][CH:34]=2)[CH2:27][CH2:28]1)([CH3:21])([CH3:19])[CH3:20]

Participants

3

Reactant 2

HCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-oneHCID 89682182HCID 89682182, compound

Product 1

HCID 68229068Tert-butyl (1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamateYield 52.1%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (830 mg, 2.7 mmol) was reacted with tert-butyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methylcarbamate (1.5 g, 4.0 mmol) to afford the desired product (670 mg, 52%) as a light brown solid: ESI MS m/z 477 [C27H28N2O4S+H]+.

Sources & evidence

ORD record
ord-df836c142700450db56a533e1457fb77
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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