4-(tert-Butoxycarbonylaminomethyl)phenylboronic acid, pinacol ester → tert-Butyl 4-(6-Fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

HRID 1853794Notes

Reaction equation

HRID 1853794 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]([F:14])=[CH:10][C:11]=1[O:12][CH3:13].CC1(C)C(C)(C)OB([C:27]2[CH:41]=[CH:40][C:30]([CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:29][CH:28]=2)O1>>[F:14][C:9]1[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]([C:27]2[CH:41]=[CH:40][C:30]([CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[CH:29][CH:28]=2)=[C:11]([O:12][CH3:13])[CH:10]=1

Participants

3

Reactant 2

HCID 34154424-(tert-Butoxycarbonylaminomethyl)phenylboronic acid, pinacol esterHCID 674487569-Bromo-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 67449397tert-Butyl 4-(6-Fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamateYield 48%

Procedure

Following General Procedure B, 9-bromo-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.50 mmol) was reacted with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate (200 mg, 0.60 mmol) to afford the desired product (100 mg, 48%) as a brown solid: ESI MS m/z 455 [C24H23FN2O4S+H]+.

Sources & evidence

ORD record
ord-dba4719609c14649a288220ae7cfa989
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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