Trimethylboroxine → (S)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate

HRID 1853854Notes

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]([C@H:22]([CH3:33])[CH2:23][N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:18][CH:17]=2)=[C:4]([O:34][CH3:35])[CH:3]=1.[CH3:36]B1OB(C)OB(C)O1>>[CH3:35][O:34][C:4]1[CH:3]=[C:2]([CH3:36])[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]([C@H:22]([CH3:33])[CH2:23][N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[CH:20][CH:21]=1

Participants

Reactant 2

HCID 574072Trimethylboroxine

HCID 86689528(S)-tert-butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate

Product 1

HCID 67447694(S)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamateYield 75%

Procedure

Following General Procedure J, (S)-tert-butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (150 mg, 0.269 mmol) was reacted with trimethyl boroxine (102 mg, 0.8 mmol) to afford the desired product (95 mg, 75%) as a brown solid: ESI MS m/z 493 [C28H32BrN2O4S+H]+.

Sources & evidence

ORD record: ord-c8a34160f7fe46709ef74adf24d7914d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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