Bis(pinacolato)diborane → HCID 67447234, compound

HRID 1853802Notes

Reaction equation

HRID 1853802 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.Br[C:36]1[C:37]2[C:38]3[CH:51]=[CH:50][S:49][C:39]=3[C:40](=[O:48])[NH:41][C:42]=2[CH:43]=[CH:44][C:45]=1[O:46][CH3:47]>>[CH3:47][O:46][C:45]1[CH:44]=[CH:43][C:42]2[NH:41][C:40](=[O:48])[C:39]3[S:49][CH:50]=[CH:51][C:38]=3[C:37]=2[C:36]=1[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 2733548Bis(pinacolato)diboraneHCID 12453839tert-butyl N-[(4-bromophenyl)methyl]carbamateHCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 67447234HCID 67447234, compoundYield 68.7%

Procedure

Following General Procedure E, tert-butyl 4-bromobenzylcarbamate (2.9 g, 10 mmol) was reacted with bis(pinacolato)diborane (2.8 g, 11 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.8 g, 9.0 mmol) to afford the desired product (2.7 g, 68%) as a brown solid: ESI MS m/z 437 [C24H24N2O4S+H]+.

Workup

  1. customto afford the crude boronic ester which

Sources & evidence

ORD record
ord-038c5ff2c8814fd38cf302eb414c0ffd
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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