4,4-Dimethylcyclohexen-1-ylboronic acid → HCID 58994512, compound

HRID 1190096Notes

Reaction equation

HRID 1190096 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH2:12])=[O:11])=[CH:4][C:3]=1Br.[CH3:14][C:15]1([CH3:24])[CH2:20][CH2:19][C:18](B(O)O)=[CH:17][CH2:16]1>CO.C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH2:12])=[O:11])=[CH:4][C:3]=1[C:18]1[CH2:19][CH2:20][C:15]([CH3:24])([CH3:14])[CH2:16][CH:17]=1

Participants

4

Reactant 2

HCID 441195554,4-Dimethylcyclohexen-1-ylboronic acidHCID 58994403HCID 58994403, compound

Product 1

HCID 58994512HCID 58994512, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared by the Suzuki coupling procedure of Example 7, step (d) using 3-(4-amino-3-bromo-phenyl)-propionamide (as prepared in Example 7, step (c), 76.0 mg, 0.351 mmol), and 4,4-dimethylcyclohexen-1-yl boronic acid (59.5 mg, 0.387 mmol). Silica gel chromatography (0-2% MeOH/DCM) afforded the title compound (79 mg, 92%) as a light brown oil. Mass spectrum (ESI, m/z): Calcd. for C17H24N2O, 273.2 (M+H). found 273.2.

Workup

  1. customThe title compound was prepared by the Suzuki coupling procedure of Example 7, step (d)

Sources & evidence

ORD record
ord-eecafe74b39a4506863fa552a76767f0
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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