Triisopropyl borate → Diisopropyl 2-chloro-4-(2-(4-methylpiperazin-1-yl)ethoxy)phenylboronate

HRID 506185Notes

Reaction equation

Br[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[CH:4][C:3]=1[Cl:18].[Li]CCCC.[B:24](OC(C)C)([O:29][CH:30]([CH3:32])[CH3:31])[O:25][CH:26]([CH3:28])[CH3:27]>>[Cl:18][C:3]1[CH:4]=[C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[CH:16]=[CH:17][C:2]=1[B:24]([O:29][CH:30]([CH3:32])[CH3:31])[O:25][CH:26]([CH3:28])[CH3:27]

Participants

Reactant 3

HCID 21531Triisopropyl borate

HCID 684633641-[2-(4-Bromo-3-chlorophenoxy)ethyl]-4-methyl-piperazine

HCID 178418339Butyllithium

Product 1

HCID 68466082Diisopropyl 2-chloro-4-(2-(4-methylpiperazin-1-yl)ethoxy)phenylboronate

Procedure

1-[2-(4-Bromo-3-chlorophenoxy)ethyl]-4-methyl-piperazine was reacted with n-BuLi at 0° C. in the presence of triisopropyl borate to give diisopropyl 2-chloro-4-(2-(4-methylpiperazin-1-yl)ethoxy)phenylboronate upon warming to room temperature.

Sources & evidence

ORD record: ord-244fd642624a43baa212d90fc9b93e33
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781591B2

Reaction notes

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