Trimethylboroxine → HCID 67449497, compound

HRID 1853816Notes

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:30]=[CH:29][C:19]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:18][CH:17]=2)=[C:4]([O:31][CH3:32])[CH:3]=1.[CH3:33]B1OB(C)OB(C)O1>>[CH3:32][O:31][C:4]1[CH:3]=[C:2]([CH3:33])[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]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[CH:29][CH:30]=1

Participants

Reactant 2

HCID 574072Trimethylboroxine

HCID 86689498HCID 86689498, compound

Product 1

HCID 67449497HCID 67449497, compoundYield 95.4%

Procedure

Following General Procedure J, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (52 mg, 0.10 mmol) was reacted with trimethylboroxine (13 mg, 0.10 mmol) to afford the desired product (43 mg, 95%) as a grey solid: ESI MS m/z 451 [C25H26N2O4S+H]+.

Sources & evidence

ORD record: ord-e2ad45b839ce4818b5a43b36a7d76d79
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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