Trimethylboroxine → tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

HRID 1853817Notes

Reaction equation

HRID 1853817 reaction equation
Br[C:2]1[C:11]2[NH:10][C:9](=[O:12])[C:8]3[S:13][CH:14]=[CH:15][C:7]=3[C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:23])=[CH:18][CH:17]=2)=[C:4]([O:32][CH3:33])[CH:3]=1.[CH3:34]B1OB(C)OB(C)O1>>[CH3:33][O:32][C:4]1[CH:3]=[C:2]([CH3:34])[C:11]2[NH:10][C:9](=[O:12])[C:8]3[S:13][CH:14]=[CH:15][C:7]=3[C:6]=2[C:5]=1[C:16]1[CH:17]=[CH:18][C:19]([CH:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:23])=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 574072TrimethylboroxineHCID 86689504tert-Butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Product 1

HCID 86689505tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamateYield 71.7%

Procedure

Following General Procedure J, tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (32 mg, 0.060 mmol) was reacted with trimethylboroxine (8 mg, 0.060 mmol) to afford the desired product (20 mg, 61%) as a grey solid: ESI MS m/z 465 [C26H28N2O4S+H]+.

Sources & evidence

ORD record
ord-14341d3b0d204ccfa98340eb8159985d
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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