9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one → Tert-butyl (1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate

HRID 1853674Notes

Reaction equation

HRID 1853674 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].CC1(C)C(C)(C)OB([C:27]2[CH:32]=[CH:31][C:30]([C:33]3([CH2:37][NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:36][CH2:35][CH2:34]3)=[CH:29][CH:28]=2)O1>>[C:41]([O:40][C:39](=[O:45])[NH:38][CH2:37][C:33]1([C:30]2[CH:29]=[CH:28][C:27]([C:2]3[C:3]4[C:4]5[CH:18]=[CH:17][S:16][C:5]=5[C:6](=[O:15])[NH:7][C:8]=4[C:9]([CH3:14])=[CH:10][C:11]=3[O:12][CH3:13])=[CH:32][CH:31]=2)[CH2:36][CH2:35][CH2:34]1)([CH3:44])([CH3:42])[CH3:43]

Participants

3

Reactant 2

HCID 674500069-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-oneHCID 86689569Tert-butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methylcarbamate

Product 1

HCID 86689520Tert-butyl (1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamateYield 45%

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 tert-butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methylcarbamate (270 mg, 0.70 mmol to afford the desired product (105 mg, 45%) as a light brown solid: ESI MS m/z 505 [C29H32N2O4S+H]+.

Sources & evidence

ORD record
ord-c373aaf326e24416856628b126b8c4e1
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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