9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one → HCID 67449989, compound

HRID 1853723Notes

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

Participants

Reactant 2

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

HCID 674507451338544-33-4

Product 1

HCID 67449989HCID 67449989, compoundYield 62%

Procedure

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (200 mg, 0.62 mmol) was reacted with tert-butyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (350 mg, 0.93 mmol) to afford the desired product (95 mg, 62%) as a brown solid: ESI MS m/z 493 [C28H32N2O4S+H]+.

Sources & evidence

ORD record: ord-da99be76281b4d3589ba808c2951d725
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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