4-Amino-3-bromobenzamide → 4-Amino-3-(4,4-dimethyl-cyclohex-1-enyl)-benzamide

HRID 1711246Notes

Reaction equation

HRID 1711246 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1Br.[CH3:12][C:13]1([CH3:28])[CH2:18][CH2:17][C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][CH2:14]1>CO.C(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[C:16]1[CH2:17][CH2:18][C:13]([CH3:28])([CH3:12])[CH2:14][CH:15]=1

Participants

4

Reactant 2

HCID 121180554-Amino-3-bromobenzamideHCID 231420132-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 587548584-Amino-3-(4,4-dimethyl-cyclohex-1-enyl)-benzamideYield 78%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared by the Suzuki coupling procedure of Example 11, step (e) using 4-amino-3-bromo-benzamide (as prepared in Example 16, step (a), 62.4 mg, 0.289 mmol), and 2-(4,4-dimethyl-cyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (75.0 mg, 0.318 mmol). Silica gel chromatography (0-2% MeOH/DCM) afforded the title compound (55 mg, 78%) as a faint yellow solid. Mass spectrum (ESI, m/z): Calcd. for C15H20N2O, 245.2 (M+H), found 245.2.

Workup

  1. customThe title compound was prepared by the Suzuki coupling procedure of Example 11, step (e)

Sources & evidence

ORD record
ord-3ca54e532cfb4baaa87bd9cbae713f31
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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