4-(tert-Butoxycarbonylaminomethyl)phenylboronic acid → tert-Butyl 4-(8-Methoxy-2-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

HRID 1853762Notes

Reaction equation

HRID 1853762 reaction equation
Br[C:2]1[C:3]2[C:4]3[CH:17]=[C:16]([CH3:18])[S:15][C:5]=3[C:6](=[O:14])[NH:7][C:8]=2[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].[C:19]([O:23][C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:8]2[NH:7][C:6](=[O:14])[C:5]3[S:15][C:16]([CH3:18])=[CH:17][C:4]=3[C:3]=2[C:2]=1[C:31]1[CH:32]=[CH:33][C:28]([CH2:27][NH:26][C:24](=[O:25])[O:23][C:19]([CH3:20])([CH3:21])[CH3:22])=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 38631634-(tert-Butoxycarbonylaminomethyl)phenylboronic acidHCID 674501169-Bromo-8-methoxy-2-methylthieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 68229071tert-Butyl 4-(8-Methoxy-2-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamateYield 57.3%

Procedure

Following General Procedure B A, 9-bromo-8-methoxy-2-methylthieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.31 mmol) was reacted with 4-[(tert-butoxycarbonylamino)methyl]phenylboronic acid (120 mg, 0.40 mmol) to afford desired product (80 mg, 55%) as a brown solid: ESI MS m/z 451 [C25H26N2O4S+H]+.

Sources & evidence

ORD record
ord-cb724ef3a3d04fcebcb36434b2939b61
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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