9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one → (R)-tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate

HRID 1853669Notes

Reaction equation

HRID 1853669 reaction equation
Br[C:2]1[C:3]2[C:4]3[CH:18]=[CH:17][S:16][C:5]=3[C:6](=[O:15])[NH:7][C:8]=2[C:9]([CH3:14])=[CH:10][C:11]=1[O:12][CH3:13].[C:19]([O:23][C:24](=[O:44])[N:25]([CH3:43])[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])([CH3:22])([CH3:21])[CH3:20]>>[CH3:13][O:12][C:11]1[CH:10]=[C:9]([CH3:14])[C:8]2[NH:7][C:6](=[O:15])[C:5]3[S:16][CH:17]=[CH:18][C:4]=3[C:3]=2[C:2]=1[C:31]1[CH:30]=[CH:29][C:28]([C@H:26]([N:25]([CH3:43])[C:24](=[O:44])[O:23][C:19]([CH3:21])([CH3:20])[CH3:22])[CH3:27])=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 674500069-bromo-8-methoxy-6-methylthieno[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 68229242(R)-tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamateYield 66%

Procedure

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with (R)-tert-butylmethyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate (250 mg, 0.69 mmol to afford the desired product (145 mg, 66%) as a light brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.

Sources & evidence

ORD record
ord-8a8e5ba989534e86bb48ac5993ac7954
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

Loading…