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

HRID 1853667Notes

Reaction equation

HRID 1853667 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])[NH:25][CH2:26][C@H:27]([C:29]1[CH:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][CH:30]=1)[CH3:28])([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:32]1[CH:31]=[CH:30][C:29]([C@H:27]([CH3:28])[CH2:26][NH:25][C:24](=[O:44])[O:23][C:19]([CH3:21])([CH3:20])[CH3:22])=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 674500069-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-oneHCID 67452222(S)-tert-butyl2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate

Product 1

HCID 67450215(S)-tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamateYield 62%

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 (S)-tert-butyl2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (251 mg, 0.69 mmol) to afford the desired product (135 mg, 62%) as a light brown solid: ESI MS m/z 479 [C27H30N2O4S+H]+.

Sources & evidence

ORD record
ord-1a290ff4175e46c69936f8d057bb554b
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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