Bis(pinacolato)diborane → Tert-butyl 2-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propan-2-ylcarbamate

HRID 1853804Notes

Reaction equation

HRID 1853804 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.Br[C:38]1[C:39]2[C:40]3[CH:53]=[CH:52][S:51][C:41]=3[C:42](=[O:50])[NH:43][C:44]=2[CH:45]=[CH:46][C:47]=1[O:48][CH3:49]>>[CH3:49][O:48][C:47]1[CH:46]=[CH:45][C:44]2[NH:43][C:42](=[O:50])[C:41]3[S:51][CH:52]=[CH:53][C:40]=3[C:39]=2[C:38]=1[C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:10])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 2733548Bis(pinacolato)diboraneHCID 18183247tert-Butyl 2-(4-bromophenyl)propan-2-ylcarbamateHCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 68229168Tert-butyl 2-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propan-2-ylcarbamateYield 52.6%

Procedure

Following General Procedure E, tert-butyl 2-(4-bromophenyl)propan-2-ylcarbamate (160 mg, 0.50 mmol) was reacted with bis(pinacolato)diboron (140 mg, 0.55 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (140 mg, 0.45 mmol) to afford the desired product (110 mg, 47%) as a brown solid: ESI MS m/z 465 [C26H28N2O4S+H]+.

Workup

  1. customto afford the crude boronic ester which

Sources & evidence

ORD record
ord-8f989e568ae44834acaa91c8b04d79aa
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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