9-Bromo-8-methoxy-2,6-dimethyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one → (R)-tert-Butyl 2-(4-(8-methoxy-2,6-dimethyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

HRID 1853823Notes

Reaction equation

HRID 1853823 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]([CH3:25])[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:11][CH:10]=2)O1.Br[C:28]1[C:29]2[C:30]3[CH:52]=[C:51]([CH3:53])[S:50][C:31]=3[C:32](=[O:49])[N:33]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:34]=2[C:35]([CH3:40])=[CH:36][C:37]=1[O:38][CH3:39]>>[CH3:39][O:38][C:37]1[CH:36]=[C:35]([CH3:40])[C:34]2[N:33]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:46])([CH3:47])[CH3:48])[C:32](=[O:49])[C:31]3[S:50][C:51]([CH3:53])=[CH:52][C:30]=3[C:29]=2[C:28]=1[C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]([CH3:25])[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 674491269-Bromo-8-methoxy-2,6-dimethyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-oneHCID 67450410(R)-tert-butyl (2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate

Product 1

HCID 67449401(R)-tert-Butyl 2-(4-(8-methoxy-2,6-dimethyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamateYield 45%

Procedure

Following General Procedure B, (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (0.12 g, 0.33 mmol) was reacted with 9-bromo-8-methoxy-2,6-dimethyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one (0.12 g, 0.33 mmol) to afford the desired product (78 mg, 45%) as a solid: ESI MS m/z 623 [C34H46N2O5SSi+H]+.

Sources & evidence

ORD record
ord-9aa8955d184e4ebb906f932cca3241d3
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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