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

HRID 1853680Notes

Reaction equation

HRID 1853680 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:45])[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][C:30]=1[F:44])[CH3:28])([CH3:22])([CH3:21])[CH3:20]>>[F:44][C:30]1[CH:31]=[C:32]([C:2]2[C:3]3[C:4]4[CH:18]=[CH:17][S:16][C:5]=4[C:6](=[O:15])[NH:7][C:8]=3[C:9]([CH3:14])=[CH:10][C:11]=2[O:12][CH3:13])[CH:33]=[CH:34][C:29]=1[C@H:27]([CH3:28])[CH2:26][NH:25][C:24](=[O:45])[O:23][C:19]([CH3:21])([CH3:20])[CH3:22]

Participants

3

Reactant 2

HCID 674500069-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-oneHCID 89676149(S)-tert-butyl2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate

Product 1

HCID 67450529(S)-tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamateYield 36%

Procedure

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (380 mg, 1.2 mmol) was reacted with (S)-tert-butyl2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (400 mg, 1.1 mmol) to afford the desired product (190 mg, 36%) as a yellow solid: ESI MS m/z 497 [C27H29FN2O4S+H]+.

Sources & evidence

ORD record
ord-707eef8a48a34c80bfebd5c113dba388
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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