9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one → (R)-tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate

HRID 1853670Notes

Reaction equation

HRID 1853670 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:43])[N:24]([CH3:42])[C@@H:25]([C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][CH:28]=1)[CH3:26])([CH3:21])([CH3:20])[CH3:19]>>[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:30]1[CH:29]=[CH:28][C:27]([C@H:25]([N:24]([CH3:42])[C:23](=[O:43])[O:22][C:18]([CH3:20])([CH3:19])[CH3:21])[CH3:26])=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-oneHCID 67454267(R)-tert-butylmethyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate

Product 1

HCID 86689443(R)-tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamateYield 68.5%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one 1.4 g, 4.4 mmol) was reacted with (R)-tert-butylmethyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate (2.4 g, 6.6 mmol) to afford the desired product (1.4 g, 66%) as a light brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.

Sources & evidence

ORD record
ord-b2e025db065d41d98faedfe5b11183df
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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