Potassium Carbonate → tert-Butyl 4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperazine-1-carboxylate

HRID 714941Notes

Reaction equation

HRID 714941 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:4][CH:3]=1.[C:17](=O)([O-])[O-].[K+].[K+].[N:23]1([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CN(C=O)C>[CH3:15][C:10]1([CH3:16])[C:11]([CH3:14])([CH3:13])[O:12][B:8]([C:5]2[CH:6]=[CH:7][C:2]([CH2:17][N:26]3[CH2:27][CH2:28][N:23]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24][CH2:25]3)=[CH:3][CH:4]=2)[O:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 107553762-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 53216820tert-Butyl 4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.114 g, 0.4 mmol) and potassium carbonate (0.060 g, 0.43 mmol) in DMF (3 mL) was added tert-Butyl 1-piperazinecarboxylate (0.071 g, 0.4 mmol) and the resulting reaction mixture stirred at room temperature for 2 hours. The solvent was removed in vacuo and the crude tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperazine-1-carboxylate obtained was used without further purification. LCMS (1) Rt: 2.56 min; m/z (ES+) 403.

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-08ba5452b75e43778a5663db44695894
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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