9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one → HCID 86689452, compound

HRID 1853682Notes

Reaction equation

HRID 1853682 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].[CH3:19][CH:20]([CH3:46])[CH:21]([C:31]1[CH:36]=[CH:35][C:34](B2OC(C)(C)C(C)(C)O2)=[CH:33][CH:32]=1)[CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]>>[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:34]1[CH:33]=[CH:32][C:31]([CH:21]([CH:20]([CH3:46])[CH3:19])[CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 674500069-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-oneHCID 86689451HCID 86689451, compound

Product 1

HCID 86689452HCID 86689452, compoundYield 15%

Procedure

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (500 mg, 1.54 mmol) was reacted with tert-butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (590 mg, 1.9 mmol) to afford the desired product (120 mg, 15%) as a yellow solid: ESI MS m/z 507 [C29H34N2O4S+H]+.

Sources & evidence

ORD record
ord-a307b4e86b714a16a504ad8a3648fc91
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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