2-Bromoethanol → 2-(4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazin-1-yl)ethanol

HRID 57563Notes

Reaction equation

Cl.[CH3:2][C:3]1([CH3:22])[C:7]([CH3:9])([CH3:8])[O:6][B:5]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[O:4]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][OH:32]>C(#N)C>[CH3:9][C:7]1([CH3:8])[C:3]([CH3:22])([CH3:2])[O:4][B:5]([C:10]2[CH:11]=[CH:12][C:13]([N:16]3[CH2:17][CH2:18][N:19]([CH2:30][CH2:31][OH:32])[CH2:20][CH2:21]3)=[CH:14][CH:15]=2)[O:6]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine hydrochloride (500 mg, 1.54 mmol) and potassium carbonate (430 mg, 3.1 mmol) in acetonitrile (20 mL) was added 2-bromoethanol (388 mg, 3.1 mmol), then the mixture was heated at 60° C. overnight under an atmosphere of nitrogen. Then the mixture was filtered over celite and washed with DCM, concentrated to give product as a light brown solid. MS (m/z): 333 (M+H)+.

Workup

filtrationThen the mixture was filtered over celite
washwashed with DCM
concentrationconcentrated
customto give product as a light brown solid

Sources & evidence

ORD record: ord-be7039892c9b4440990e7bc0b5df7e29
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434726B2

Reaction notes

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