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

HRID 1853665Notes

Reaction equation

HRID 1853665 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])[N:24]([CH3:43])[CH2:25][C@H:26]([C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][CH:29]=1)[CH3:27])([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:31]1[CH:30]=[CH:29][C:28]([C@H:26]([CH3:27])[CH2:25][N:24]([CH3:43])[C:23](=[O:44])[O:22][C:18]([CH3:19])([CH3:21])[CH3:20])=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-oneHCID 67452101(S)-tert-butylmethyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate

Product 1

HCID 67447279(S)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamateYield 50%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.5 g, 8.1 mmol) was reacted with (S)-tert-butylmethyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate (4.6 g, 12 mmol) to afford the desired product (1.9 g, 50%) as a light brown solid: ESI MS m/z 47 [C27H30N2O4S+H]+.

Sources & evidence

ORD record
ord-5249b32681214ab981faef4ae1fcd6a1
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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